We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation rentals in Squirrel Island, ME and nearby

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 98 Rentals in the Squirrel Island Area
loading...
Sort by

The following rentals are within 10 kilometres of Squirrel Island, Maine.

From
$143
Per Night
View Details
1 / 19
Payment Protection
Boothbay
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (5) Make Enquiry
From
$163
Per Night
View Details
1 / 14
Payment Protection
Boothbay Harbor
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Enquiry
From
$869
Per Week
View Details
1 / 14
Payment Protection
Boothbay Harbor
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (2) Make Enquiry
From
$151
Per Night
View Details
1 / 19
Payment Protection
South Bristol
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Cottage overlooking picturesque harbor in the authenic Maine community of South Bristol. Perfect for small family or couple who enjoy waterviews and easy access to provisions and fresh lobster. Good location for walks to picnic spots and Christmas Cove, as well as short drives to Pemaquid,... View all property information
Make Enquiry
5 of 5 stars Reviewed 24 August 2014
The cottage is located in a quaint, quintessential Maine community. It is a pretty, sleepy town with limited resources, but you can find anything you might need in the three...
See all reviews
From
$250
Per Night
View Details
1 / 24
Payment Protection
Boothbay Harbor
3 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (15) Make Enquiry
Amenities & Details
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Our log cabin is nestled in the Sprucewold Community, about a 5 minute walk to a beautiful beach and a 10 minute walk to downtown Boothbay Harbor. It is a spacious 2 bedroom + loft cedar log cabin that was recently redone with brand new floors, a screened in porch, and bathroom. We have a fully... View all property information
Make Enquiry
4 of 5 stars Reviewed 2 September 2014
We found the cabin extremely quaint and accommodating. We enjoyed morning coffee on the screened in porch and made use of comfortable living room in the evenings. The owner was...
5 of 5 stars Reviewed 5 August 2014
This was our second year renting from the Taylors in their gorgeous cedar log cabin in Boothbay Harbor. It was great to be familiar with it, and to anticipate all that we were...
See all reviews
From
$240
Per Night
View Details
1 / 7
Boothbay
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The family who own's Crow's Nest have enjoyed spending many happy vacations here and cherish the simplicity of the cottage as a way to get away from the hustle and bustle of their busy lives. The main cottage is undergoing renovations and new photos will be posted as available. The Guest Cottage... View all property information
Make Enquiry
From
$169
Per Night
View Details
1 / 10
Payment Protection
East Boothbay
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Grill
  • Internet Access
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Oceanfront 2-bedroom cottage in East Boothbay with large deck overlooking water. This quintessential Maine cottage features a panoramic view of the water, of sunrises, and of the moon reflecting on the water. Built in the 1950s, this 2 bedroom cottage sleeps 6 (queen bed, full bed and pull-out... View all property information
Make Enquiry
5 of 5 stars Reviewed 4 September 2014
A comfy and clean cottage .Has a large deck with a spectacular view of the water. My sister and I spent our evenings sipping wine and listening to the waves lap against the rocks...
4 of 5 stars Reviewed 7 July 2014
Nice ocean view. Great location, not far from Boothbay Harbor, Pemaquid Lighthouse, and other main harbors and sights. Nice setup for a quick getaway. Clean and pet...
See all reviews
From
$250
Per Night
View Details
1 / 20
Payment Protection
South Bristol
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
South Bristol/Christmas Cove Cottage Classic cottage in picturesque Christmas Cove on Rutherford Island has new amenities yet retains its charm as a shipbuilding captain's home built in the 1840's. The home has recently been remodeled and updated with a large eat-in gourmet kitchen and... View all property information
Make Enquiry
From
$5,628
Per Week
View Details
1 / 27
Bayville
6 Bedrooms, 4 Bathrooms, Sleeps 14
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This historic cottage, once used to house visitors who arrived at the steam ship landing nearby, now offers a fantastic spot for a large family get-away. The large house boasts enough space to sleep 14 people while offering the most wonderful outdoor accommodations! The living room opens up to a... View all property information
Make Enquiry
From
$1,188
Per Week
View Details
1 / 5
Payment Protection
Boothbay Harbor
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
On the quiet East Side, perched on a hill overlooking the harbor this stand alone apartment brings the world of boating in Maine right before your eyes. In addition to enjoying views from inside, you have two decks to enjoy outside. Everything is included in the weekly rental..(sat-sat)... View all property information
Make Enquiry
Get the List
From
$2,501
Per Week
View Details
1 / 4
Payment Protection
East Boothbay
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Ocean Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This Cotttage is located on Ocean Point, Mane. It is near Grimes Cove Beach where you can swim, sail, kayak or just enjoy the view. It's up to you if you want to launch or just kick back. Great place for a family getaway or couples retreat, just bring yourself and your imagination. View all property information
Make Enquiry
From
$1,688
Per Week
View Details
1 / 15
Payment Protection
Boothbay
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Water Views
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
New for 2015 PERFECT for a family or group of friends to enjoy a vacation that gives you the peace and quiet and yet only minutes away from town. Enjoy the lake with it's tranquil morning peace and quiet as you enjoy the sunrise and loons on the water swimming by, or the enjoy sunsets as you lounge... View all property information
Make Enquiry
From
$295
Per Night
View Details
1 / 44
Payment Protection
Boothbay Harbor
5 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Ocean Views
  • Private Fishing...
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This lovely revolutionary war era cape-style house has a large central chimney, original pine floors, exposed beams and other period details. Electric wiring and indoor plumbing were added sometime in the last century -- this house is simple, authentic and quaint, not modern or luxurious. With... View all property information
Make Enquiry
From
$938
Per Week
View Details
1 / 7
Payment Protection
Boothbay Harbor
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Washer
  • Water Views
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Lakeside Cottage Lakeside Cottage is a compact bright and cheery one bedroom cottage overlooking Appalachee Lake. Grill dinner on the deck while enjoying the sunset over the lake. Relax in the open living/dining/kitchen area and be taken in by the lake views from the extensive windows. Watch... View all property information
Make Enquiry
From
$1,392
Per Night
View Details
1 / 35
Boothbay
8 Bedrooms, 3 Bathrooms, Sleeps 16
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
CAPTAIN’S QUARTERS Walk out the door, across the lawn and be on the water. Just like that. Sailing, swimming, kayaking, fishing, boating –right from your own dock & float. Captain’s Quarters is for anyone who loves the ocean and all things nautical! Located on the ocean side of Linekin Bay, just... View all property information
Make Enquiry
From
$156
Per Night
View Details
1 / 13
Payment Protection
Boothbay Harbor
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Make Enquiry
Amenities & Details
  • Balcony
  • Grill
  • Housekeeping...
  • Internet Access
  • Safe
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This 1800s schoolhouse is full of charm! Gleaming wide pine floors and beamed ceilings add to the appeal. The home's location is truly what makes it exceptional. Walk 1 minute to the harbor or to our favorite breakfast spot. A 4 minute walk takes you to all Boothbay Harbor has to offer--shops,... View all property information
Make Enquiry
From
$411
Per Night
View Details
1 / 7
Payment Protection
Boothbay Harbor
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This will be filled in later View all property information
Make Enquiry
From
$1,126
Per Week
View Details
1 / 12
Payment Protection
Southport
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
the cottage is on a 50 foot bluff, western exposure facing the atlantic ocean. it has a low water beach. its a comfortable cottage with all the amenties 2 bedrooms - 4 twin beds, 2 beds per room kitchen stove, refrigerator, microwave dining room living room fireplace, tv, radio... View all property information
Make Enquiry
From
$219
Per Night
View Details
1 / 9
Payment Protection
Boothbay Harbor
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Two bedroom log cabin: Cable TV, DVD Player, Sterio CD player, wireless internet, mini bar, washer+dryer, picnic table, barbecue grills. If you wanna book right away please call: 207-215-7098 Anytime, thank you for you booking, see you soon. View all property information
Make Enquiry
From
$547
Per Night
View Details
1 / 35
Southport
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
PIFFI BIFF Piffi Biff is a beautiful cottage located on the historic Southport Island on the Boothbay peninsula. With incredible views of the Atlantic Ocean, Squirrel Island, Boothbay Harbor, Burnt Island, you will also see porpoises, whales, migratory shore birds, sailboats, yachts and lobster... View all property information
Make Enquiry
From
$572
Per Night
View Details
1 / 22
Payment Protection
Southport
6 Bedrooms, 6 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Coveside House, a Sea Captain-style home overlooking Decker's Cove,is located on beautiful Southport Island on the coast of Maine, just an hour's drive from Portland, and minutes from Boothbay Harbor. This coastal home is approximately 140 years old having gone through several transformations and... View all property information
Make Enquiry
From
$313
Per Night
View Details
1 / 23
Payment Protection
Boothbay Harbor
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
This oceanfront cottage is ideal for one or two people. It is fully self contained having everything you need for a memorable vacation. An amazing sunrise greets you each morning. It is quiet and and peaceful place as you sip your morning coffee on the porch which overlooks world famous Cabbage... View all property information
Make Enquiry
From
$163
Per Night
View Details
1 / 10
Payment Protection
Boothbay Harbor
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Private Fishing...
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
This beautiful, rustic cabin sits on a peninsula of Big Knickerbocker Lake and is the perfect choice for those seeking seclusion and privacy. Surrounded by old oak trees and water on three sides, this classic Maine hideaway was built by local craftsmen using reclaimed wood from a nearby antique... View all property information
Make Enquiry
From
$1,563
Per Week
View Details
1 / 12
Payment Protection
Boothbay Harbor
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Ocean Views
  • Private Fishing...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Oceanview Cottage Beautiful 2 bed, 2 bath overlooking Linekin Bay in Boothbay Harbor area. Each bedroom has abundant closet and dresser space as well as a private bathroom and windows that assure good nighttime breezes. One room has twin beds that easily convert to a king, and the other has a... View all property information
Make Enquiry
From
$473
Per Night
View Details
1 / 23
Boothbay Harbor
4 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (1) Make Enquiry
Amenities & Details
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
LAZY DAYS For boaters, Spruce Point is the entrance to Boothbay Harbor. Lazy Days is the perfect spot to watch the ‘commuters’ come and go! From your private water-side deck, you have one of the best views around. Relax with a cocktail as the sun goes down for spectacular sunsets, swim from the... View all property information
Make Enquiry
4 of 5 stars Reviewed 10 August 2013
This was our second stay at this house? It is a great house for our family with four children and a dog. They loved being able to swim right outside at the small cove. They...
See all reviews
From
$298
Per Night
View Details
1 / 12
Boothbay
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Come spend your days enjoying the beautiful water views, while sitting on the deck and watching the activity in the Cove and the birds flying about. A wonderful spot for canoeing/kayaking, as a canoe is included with your rental! This clean, comfortable two bedroom cottage has an eat-in kitchen... View all property information
Make Enquiry
4 of 5 stars Reviewed 3 August 2014
My family and I have vacationed in the Boothbay Harbor/Southport area for the past 30 years. When our regular rental spot on Newagen wasn't available, we aggressively began a...
See all reviews
From
$269
Per Night
View Details
1 / 10
Boothbay Harbor
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
THREE SEAS Perfectly located on McKown’s Point and part of the Juniper Point Association this beautifully quaint little two bedroom cottage is the perfect family retreat for your summer vacation! Enjoy views of Mouse and Squirrel Island from the living room windows and grassy yard. Open the windows... View all property information
Make Enquiry
5 of 5 stars Reviewed 28 September 2014
We love comming to this cottage. It is one of the most relaxing places on earth. It has all the conviences of home with none of the stress. Close enought to loads of attractionsto...
See all reviews
From
$658
Per Night
View Details
1 / 31
Southport
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
FROSTY GLENN Launch your kayak at the nearby town dock or from the cottage seaside shoreline (rocky), then paddle out around Cuckolds Lighthouse and Cape Island. Take an icy dip in the Atlantic from the rocky shore. Walk. Commune with nature. Meet the locals. Enjoy all this beautiful seaside... View all property information
Make Enquiry
From
$532
Per Night
View Details
1 / 31
East Boothbay
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (3) Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
THE VILLA Views, views and more views are what make this cottage so popular. Everywhere you look you see ocean. From the kitchen, the dining room, the living room, the bedrooms, the screened in porch. is there for you as you lay in bed and look out the windows, prepare dinner in the kitchen, while... View all property information
Make Enquiry
5 of 5 stars Reviewed 18 July 2014
This cottage is has panoramic views of the beautiful Maine coast. Large enough for three families and children, this is a well stocked home with loads of amenities. One whole...
2 of 5 stars Reviewed 12 August 2013
Although we knew that this property was old, we did not expect it to be dirty and lacking in some of the commonly provided amenities, like toilet paper. The bedroom carpeting is...
See all reviews
From
$530
Per Night
View Details
1 / 16
Boothbay Harbor
5 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
JOHN’S COTTAGE Floor to ceiling widows with views of Mouse and Squirrel Islands and a wrap-around porch with sections that are screened, glassed and open air! Beautifully tended grounds. 100 feet of shoreline. Access to Association beach, dock and float. McKown Point is one of the most beautiful... View all property information
Make Enquiry
From
$313
Per Night
View Details
1 / 65
Boothbay
10 Bedrooms, 9 Bathrooms, Sleeps 20
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Children's Pool
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Come away from it all--catch your breath. Six miles from the bustle of Boothbay Harbor is a peaceful 15 acre river-front retreat, set among rolling lawns, meandering stone walls, apple orchards and richly colored perennial gardens. The estate consists of four New England-style buildings: one... View all property information
Make Enquiry
5 of 5 stars Reviewed 3 September 2014
We were 5 couples visiting for Labor Day weekend (3 nights) and we all had more than enough room to amble around in this very spacious and homey farm house. Melissa is very...
5 of 5 stars Reviewed 25 August 2014
The Farmhouse is a fantastic house. Truly a home away from home. My teenage daughter exclaimed, "this place is awesome!" Everyone was very comfortable and happy with their own...
See all reviews
From
$344
Per Night
View Details
1 / 24
Southport
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Ocean Views
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Imagine sunrise breakfast, sunset dinners, and in between, life on the edge...the oceans edge! Our quaint Captains Cottage has all the warmth and comforts of home with an everchanging view! The first level includes, livingroom, 2 bedrooms, fully equipped kitchen, diningroom and bathroom. Off the... View all property information
Make Enquiry
From
$361
Per Night
View Details
1 / 22
East Boothbay
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
THE HAVEN Once owned by local author Dr. A. Power Davies, this Classic Maine vacation cottage is where another noted author, Thomas Wolfe, edited “Look Homeward Angel”. In the collection of his personal writings he mentions his stay here in Ocean Point in letters to his mother. Facing Negro Island... View all property information
Make Enquiry
From
$1,876
Per Week
View Details
1 / 22
Boothbay Harbor
4 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (1) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
An On the Water in Maine 'Top 10' property, this classic 1907 cottage is a perfect combination of traditional Maine charm and modern amenities. The Jones cottage had a major kitchen renovation in 2014, and has undergone upgrades including new furnishings, two remodeled bathrooms, modern appliances,... View all property information
Make Enquiry
4 of 5 stars Reviewed 15 August 2014
Nice cabin feel with plenty of room inside and a nice big fenced in porch. The building was built in the early 1900's and still retains the old visible knob and tube wiring which...
See all reviews
From
$423
Per Night
View Details
1 / 15
East Boothbay
4 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This classic log cabin, with its new private deepwater dock and float great for putting in the 2 kayaks that come with this rental, faces west and overlooks Linekin Bay. The cabin welcomes you with patches of day lilies and other wild flowers. Enjoy the views while dining from a screened porch or... View all property information
Make Enquiry
From
$2,189
Per Week
View Details
1 / 11
Boothbay Harbor
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Bayville Cottage is a furnished 3 bedroom, 1.5 bath vacation rental home on the shores of the quiet and picturesque Linekin Bay in Bayville, Maine, just minutes from the buzzing little downtown of Boothbay Harbor, where you can take in Lobster, drinks at McSeagull's, stroll through several art... View all property information
Make Enquiry
5 of 5 stars Reviewed 24 September 2014
It's not often you find a perfect vacation home. There's always something missing, a less than perfect view, noisy neighbors or an inconvenient location. NOT HERE! There are 3...
See all reviews
From
$313
Per Night
View Details
1 / 26
Boothbay Harbor
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (4) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Ever wonder what it would be like to live on the edge of a true working waterfront? To watch a thriving harbor community go about everyday life and feel like you’re a part of it? You can – by spending your vacation in the heart of Boothbay Harbor, Maine! Wake to the rising sun on the front porch... View all property information
Make Enquiry
From
$205
Per Night
View Details
1 / 12
Boothbay Harbor
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Reviews (11) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Portside is a year-round luxury condo with the charm of a cottage in the heart of historic Boothbay Harbor, Maine. The cottage is in the town center and yet you will find tranquility and privacy inside. We share a dock and float with the other two Back Bay Cottage units and have our own deck on the... View all property information
Make Enquiry
5 of 5 stars Reviewed 2 July 2014
My family recently spent the week in the Portside condo and had such a fabulous time. The condo is beautifully furnished and maintained and right on the water. It is within...
5 of 5 stars Reviewed 17 June 2014
This lovely waterfront condo was cozy, comfortable, beautifully furnished, and very well equipped. It was so convenient to the shops and restaurants in the Boothbay Harbor area. A...
See all reviews
From
$1,626
Per Week
View Details
1 / 37
South Bristol
5 Bedrooms, 2 Bathrooms, Sleeps 9
Details Reviews (5) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Gym
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Sea captain's house on harbor in South Bristol.Maine, 75 feet from the water complete with porches, gardens, and chickens. The house is ideal for multi-generational groups with its first floor bedroom and bath, separate from the main part of the house. Private yard with vegetable and ornamental... View all property information
Make Enquiry
From
$1,501
Per Week
View Details
1 / 32
East Boothbay
5 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Located near the Ocean Point area of East Boothbay, and on the Little River, Rip's View is in a quiet cove just off the bold Atlantic Ocean. Renovated in 2014, Rip's View has a new master bathroom, new carpets, and new bedding. Down a long private driveway - Rip's View sits high above the cove with... View all property information
Make Enquiry
From
$413
Per Night
View Details
1 / 22
Boothbay
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
A FAIRVIEW Location, location, location! Close to the water with an amazing, unobstructed westerly view, the cottage is in a peaceful out-of-town spot on Barter’s Island. Only 2.5 miles from the Coastal Maine Botanical Garden, closer still to Porter Preserve, Fairview is an easy drive to grocery... View all property information
Make Enquiry
5 of 5 stars Reviewed 20 September 2014
We rented this wonderful cottage at the very last minute when another rental fell through. And to be honest, I'm so glad the other rental fell through! This home was perfect for...
See all reviews
From
$188
Per Night
View Details
1 / 27
Boothbay Harbor
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (37) Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Internet Access
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
At Sunny Woods House, the living and dining space, kitchen, dedicated office, media room, 2-3 bedrooms and 2 full bathrooms are all on one level—no stairs! You will find everything you'd expect to find in a modern year-round house: fully-equipped kitchen (including a dishwasher), washer and dryer,... View all property information
Make Enquiry
5 of 5 stars Reviewed 8 October 2014
We rented Lakeside Cottage for a week's holiday. It was a perfect location, with a beautiful lake at the front door, and the ocean behind us. Easy drive to town and in fact to all...
5 of 5 stars Reviewed 2 July 2014
We stayed in the Lake View Cottage. The description doesn't do it justice and we loved it up there. Our son was especially excited that the beach was right across the way and that...
See all reviews
From
$475
Per Night
View Details
1 / 21
Boothbay Harbor
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
SALTAIRE Head down to the ocean from your front porch and enjoy your private dock and float right on Linekin Bay. Or, head to the end of your driveway and enjoy a shared sandy beach at the freshwater Appalachee Lake! Saltaire is the perfect location for the best of both worlds. With all that water,... View all property information
Make Enquiry
5 of 5 stars Reviewed 27 July 2014
This was our 2nd time here at Saltaire - and loved it again!! We were here 2 yrs ago with our 11 month old, and this time traveled with our 1yr and 3yr old children. A wonderful...
See all reviews
From
$469
Per Night
View Details
1 / 15
East Boothbay
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
DASH INN A beautiful salt-water cove is fed by the tides and Little River. This is a magical spot that will steal your heart and keep you coming back year after year. You won't want to 'dash' anywhere after you arrive at this incredible cove-side retreat. The wall of windows draws the outside in.... View all property information
Make Enquiry
5 of 5 stars Reviewed 11 August 2013
3 bedrooms and 2 baths on two floors. A very private master suite on the bottom floor. Two fireplaces kept us cozy.
See all reviews
From
$224
Per Night
View Details
1 / 7
East Boothbay
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Fireplace
  • Grill
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This classic turn of the century winterized cottage is situated on the beautiful shores of Linekin Bay. East Boothbay is just three miles from the town of Boothbay Harbor but a century apart in terms of hustle and bustle. The Cottage is on Paradise Point Road which is a very private setting on... View all property information
Make Enquiry
From
$625
Per Night
View Details
1 / 18
Boothbay
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Newagen Cove Cottage is a three-bedroom cottage with a guest house (called Camp David) on Southport Island in the village of Cape Newagen. Built in 1928, this two-story, 2,500 square foot home is light and bright with lots of windows, a living room with cathedral ceiling and panoramic views. With... View all property information
Make Enquiry
From
$540
Per Night
View Details
1 / 15
Boothbay
5 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
ISLAND VIEW From the water, the giant sunroom stretched across the front of this beautiful home is a recognizable landmark! From inside the home, it is pure indulgence! Bringing the spectacular views of ocean and islands into the home, you will fall in love this amazing cottage, aptly named Island... View all property information
Make Enquiry
From
$286
Per Night
View Details
1 / 17
Boothbay Harbor
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Beautiful oceanfront property at the head of the harbor. Bright open concept kitchen/living/dining room with abundant natural light. Two cheery bedrooms, with nautical themes and one convertible sofa sleep up to six. One and a half baths include a new stackable washer and dryer. A balcony off the... View all property information
Make Enquiry
4 of 5 stars Reviewed 14 September 2013
We spent a week in August at this property, We enjoyed the ability to walk to the shops and for meals to the local restaurants just a short distance away. Absolutely loved the...
2 of 5 stars Reviewed 3 July 2012
I have stayed in several rental properties year after year and I have never quite had an experience like this one - in fact all my other experiences have been positive. The condo...
See all reviews
From
$328
Per Night
View Details
1 / 12
Boothbay Harbor
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Perched hillside, this updated older two story home is just a short walk to downtown Boothbay Harbor, with all of its restaurants, shops, and activities. Rent a kayak to explore the Harbor or go on a Whale Watch. Go deep sea fishing or sail on one of the windjammers, all accessible by foot! No... View all property information
Make Enquiry
1 of 5 stars Reviewed 2 September 2014
This rental was the worst. I have rented all over the United States, from condos, houses, to rooms within a house. This was the worst value in my experience. The check-in and...
2 of 5 stars Reviewed 13 September 2013
As timeshare owners, my husband and I travel often and stay at many beautiful resorts. Our trip to Maine was a family affair and we did not have a timeshare in Boothbay, Maine so...
See all reviews
Enquire for rates
1 / 16
Southport
4 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Early 1800's Maine home on Cosy Harbor with a shared dock and float. You are welcome to share our 2 kayaks when available. The dock is tidal, but has water around it most of the tide(8'at high tide). Walk to the Southport Yacht Club, Beaches, or the General Store for ice cream. The yacht club... View all property information
Make Enquiry
Go to map view
Book Online(21)
Use filters to find the best results!

Suitability

  • Wheelchair access (2)
  • Elder access (12)
  • Suitable for children (8)
  • Pet friendly (35)
  • Smoking allowed (0)

Amenities

  • Grill (66)
  • Other outdoor space (66)
  • Internet (47)
  • Parking (30)
  • Fireplace (29)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities