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Chatham Cheap Vacation Rental Deals

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    Travellers to Chatham are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    114 Matching Rentals in ChathamView all 459 rentals
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Apartment on the Charles River in Newton with great views, boathouse with kayaks and canoes for use. Near Brandeis, Boston College, Newton Wellesely Hospital, Newton Marriott, Routes 128 and Mass Pike The space This is a downstairs apartment with a large fireplaced living room/bedroom. There is a...
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    Chatham, Cape Cod 02633
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Pleasant Forest Shores cottages #2 : So. Chatham1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed September 22, 2017
    I admit I ended up here somewhat by accident, but it was a fortuitous accident. Not only is this small cottage colony (5 cottages) perfectly located to get to a variety of...
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    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
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    South Chatham, Chatham 02659 1525
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Cape Cod Pine Grove Cottage - 1/2 mile from beach!1 / 15
    (6)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Reviewed September 1, 2014
    We loved being so close to Cockle Cove Beach. The outside shower was a hit, too. My two teenaged boys loved, loved, loved this place. It would be even better if it had wifi.
    Reviewed August 25, 2014
    I was so happy with our stay! the cottage was very cute and was just enough room! it was close to just about anything you can want to do in the cape. the welcome gift was very...
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    About this property
    This immaculate two-bedroom/one-bath cottage sleeps five and is cozy and affordable. It's located one-half mile from Cockle Cove Beach on warm Nantucket Sound. Situated on a quiet cul de sac with a nearby childrens playground, this property is protected and cooled by pine trees and salty breezes....
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Pleasant Forest Shores cottages #3 : So. Chatham1 / 14
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed September 11, 2017
    Our stay at Pleasant Forest Shores was awesome! The cottage was very clean, had a sizable living room & kitchen and was located within a quiet neighborhood. It was also about...
    Reviewed July 1, 2017
    We actually stayed in cottage #2 but they appear to fairly similar. I used to vacation in Chatham as a kid in the late 60's and early 70's. These cottages are VERY reminiscent...
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    About this property
    Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shores just may be the place for...
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    South Chatham, Chatham 02659 1525
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    About this property
    Featuring gorgeous gardens and outdoor spaces to explore, a luxurious and updated interior, and all the comforts of home, this beautiful rental has it all! Ideal for two guests, this would be a fantastic place for a honeymoon, couples getaway, or even a relaxing solo retreat. Nestled in a quiet...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    393 STONY HILL ROAD CHATHAM Charming and completely renovated cottage, 7/10 of a mile to Scatteree Beach and the Cow Yard Landing and under 2 miles to Main St., Chatham for shopping, dining, and ice cream! This adorable one bedroom, air conditioned cottage has vaulted ceilings, exposed beams, a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Conveniently located in South Chatham, this lovely Townhouse is close to some of Chatham's best swimming beaches. A quick drive in either direction can transport you off to the quaint villages of Chatham or Harwichport for some of the Cape's best dining and shopping. This 2-bedroom, 1.5 bath end...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    62 PATUXET TRAIL Sweet cottage close to Cockle Cove Beach in South Chatham. Sleeps 5. First bedroom 1 Double, 2nd bedroom 2 twins, 3rd bedroom 1 twin. $950 off season and $1200 in season * $100 Handling Fee * choice of $55 Damage Insurance or $350 Security Deposit Please contact Courtney...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    CONDO NEXT TO COCKLE COVE BEACH IS JUST 0.9 MILES AWAY!1 / 17
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Reviewed August 18, 2014
    rental was everything we expected. Place was clean and in a great location. There were bikes, boogie boards and beach chairs for your use.
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    About this property
    Cockle Cove Beach is just 0.9 miles away from this light & bright Chatham Condominium located at Cockle Cove Ridge. The Chatham Village center is just 3 miles away for shopping, dining, Chatham A's baseball games, & the bandstand. The entry level of this 2 bedroom, 2 bath home features a living...
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    Chatham, Cape Cod 2659
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Breathtaking riverfront dog-friendly home w/ a lovely deck, close to the beach!1 / 29
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed September 29, 2017
    Very nice Chatham, Cape Cod home with great views, and not too far from town. A comfortable home that I would rent again, and the managment company was good about staying in...
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    About this property
    Experience a glimpse of Cape Cod waterfront living at this three-bedroom Chatham home, a dog-friendly property with a wrap-around deck, panoramic views of the ocean and Oyster River, and nearby access to Harding's Beach. This quaint two-level home is scenically situated between Nantucket Sound and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wouldn't you like to spend some time at this adorable updated Cape Cod Vacation Rental cottage in Chatham? It is in a convenient location with a path at the end of the road to Forest Beach. It is also just a short walk to Pleasant Road Beach. The bike trail is just off Route 28 on the corner of...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Quiet Lakeside Cottage - Ideal for Couple1 / 28
    (16)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Reviewed October 2, 2017
    This was my second time staying at Helene's cottage with my boyfriend. We loved the location — a short drive or bike ride to many nice beaches, nature walks, and main street in...
    Reviewed September 19, 2017
    I have been a repeat renter of this property for the last fifteen years. I have always found this cottage clean and a relaxing place to stay.Yearly, I notice upgrades e.g. the...
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    About this property
    At this quiet lakeside cottage you can experience classic Cape Cod with all the modern amenities -- wireless internet, cable TV, air conditioning. Enjoy beautiful sunsets as well as swimming and canoeing at the lake---and only be a short trip to the beach or Chatham center. The cottage features...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Cute cottage only 1 mile to Hardings Beach! 2 bedroom, 2 bath Cape Cod Cottage! Well maintained and appox. 1 mile to Hardings Beach in Chatham. Relax and dine in the screened porch which expands across the front of the cottage. This neighborhood is located off Barn Hill and a short distance to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 8 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1,675 per week Off-Season: $975 per week Click for More Photos, Map, and Availability Calendar Light and bright 4 bedroom home on quiet cul-de-sac in South Chatham. Comfortable furnishings throughout. Large upstairs bedrooms offer extra seating...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    3 Bedrooms, Sleeps 6 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1800 per week Off-Season: $1000 per week Weekly rentals from mid-JUNE to mid-SEPT Click for More Photos, Map, and Availability Calendar Cute 3 bedroom ranch, walking distance to town and Oyster Pond. A great new 2nd family room just finished in...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Come stay at: Misty Meadow! Enjoy this lovely condo with all amenities including Central AC mini splits and free WiFi Conveniently located too. Situated in a very quiet area of North Chatham offering private conservation views from this charming one bedroom, first floor, end unit condo. An open...
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    North Chatham, Chatham 02650
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, Sleeps 4 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1300 per week Off-Season: $1000 per week Click for More Photos, Map, and Availability Calendar Adorable one bedroom unit just steps to Lighthouse Beach! A quick walk to downtown Chatham for dinner, shopping and more, this charming condo is...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, Sleeps 4
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    3 Bedrooms, Sleeps 6 Quick View
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1775 per week Off-Season: $1050 per week Click for More Photos, Map, and Availability Calendar Weekly rentals from mid-JUNE to mid-SEPT This three bedroom home is a stones throw from Chatham's bike trail, so you can ride from your home all over...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    19 Glendon Way, S. Chatham Casual knotty pine summer cottage just 1/2 mile to Pleasant Street Beach. This 3BR/1BA single level cottage is located in a nice quiet neighborhood of South Chatham. Convenient to shopping - just a 10 minute drive into town. $1000 per week * $100 Handling Fee * Choice of...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, Sleeps 4 Quick View
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    2018 Rental Rate: $1325 per week, including the cleaning fee ~~~ Off-Season: $1075 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming cottage in the woods and only 2 minutes to Oyster River Public Boat Landing. Small screened-in porch attached. A great vacation...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Welcome to Long Camp in Chatham! Pet Friendly! Come and enjoy a cozy vacation rental cottage on Goose Pond in Chatham.  Goose Pond is the largest pond in Chatham and has 38 acres of unspoiled fresh water that is perfect for swimming, canoeing and kayaking.  Nestled on the sandy beach- This cottage...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    This traditional two bedroom, one bathroom Cape Cod cottage is just .4 miles from popular Ridgevale Beach. This one floor cottage has open dining and living rooms (new couch and chair coming for 2018) with flat screen TV, small kitchen with new stove for 2018, bathroom with shower stall, and two...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    This newly listed, cozy Chatham cottage is just steps away from the Old Colony Rail Trail. There are two bedrooms, one with a double sized bed and a/c unit, and the second with two twins. There is also a full bath with tub/shower combination. This cute cottage features one level living and an open...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1325 per week Off-Season: $1075 per week Click for More Photos, Map, and Availability Calendar Weekly rentals from mid-JUNE to mid-SEPT Quaint two bedroom cottage surrounded by beautiful gardens! Located in lovely North Chatham, this little...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This impeccable 2 bedroom and 1 bath cottage in Chatham is close to beaches, town, great restaurants, and unique shops. But you will be insulated from the summer crowds the moment you arrive at Waterview Colony, a serene retreat set on 5.5 acres with a private beach on White Pond. Recently...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, Sleeps 2 Quick View
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    2018 Rental Rate: $1100 per week including the cleaning fee ~~ FRIDAY to FRIDAY~~ Off-Season $1000 per week, including cleaning fee Click for More Photos, Map, and Availability Calendar Charming brand new cottage located just steps from Main St and the beaches of Shore Rd! Centrally located, it...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 1 Bedroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Whether you're settling in for a sun-filled beach vacation or seek a quiet seaside escape over the cooler months, this picturesque 3BR/2BA home promises a charming and relaxing stay on the Cape year-round. Spanning two floors, this stylish home features beautiful pine floors and modern decor with...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1700 per week Off-Season: $1150 per week Click for More Photos, Map, and Availability Calendar Charming and updated ranch, located in a quiet neighborhood but is also a quick drive to the warm waters of Cockle Cove Beach! This light and bright...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    #602: Make memories in this Chatham beach home within steps to Nantucket Sound!1 / 32
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed September 24, 2017
    Would totally stay here again. Super clean & comfy, plenty of room for 3 adults & a dog, nice quiet neighborhood with friendly neighbors, close to beach. Had one small...
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    South Chatham, Chatham 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Welcome to: Cape Cranberry! Quintessential Cape Cod Vacation Rental Cottage in Chatham on the way to Cockle Cove Beach. Enjoy this Cape Cod beach cottage with casual coastal decor. AC units in living area and bedrooms and free WiFi too. This home offers 2 bedrooms and a full bath with...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    About this property
    Beach-going families will find a welcoming retreat at this three-bedroom South Chatham home, a darling Cape Cod escape with a private deck and patio, a fenced yard, and a wonderful location within a short walk of the beach! This classic home sits a block off Main Street in South Chatham, just...
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    South Chatham, Chatham 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $1950 per week ~ FRIDAY TO FRIDAY Off-Season: $1250 per week Click for More Photos, Map, and Availability Calendar Charming cottage just steps to Ridgevale Beach. Upstairs addition is fabulous. It has a separate bathroom and sitting area with...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, Sleeps 6
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    2018 Rental Rate (Cleaning Fee Included): In-Season: $1225 per week Weekly rentals from mid-JUNE to mid-SEPT Click for More Photos, Map, and Availability Calendar Nicely decorated house on a quiet street near town and the Cape Cod Rail Trail. This is a very well maintained and comfortable home with...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, Sleeps 5
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1850 per week Off-Season: $1250 per week Click for More Photos, Map, and Availability Calendar Light and bright home located close to downtown and the Chatham Bike Trail, as well as the middle school tennis and basketball courts. It is an easy...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, Sleeps 6
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1800 per week Off-Season: $1250 per week Click for More Photos, Map, and Availability Calendar Beautifully remodeled home situated in a quiet yet central area of Chatham, close to everything! Updated furnishings and appliances, as well as fresh...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, Sleeps 8 Quick View
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    About this property
    2018 Rental Rates (Cleaning Fee Included): In-Season: $1675 per week Off-Season: $1275 per week Click for More Photos, Map, and Availability Calendar Adorable, updated rental located on a quiet street in South Chatham. New furnishings and fresh paint make this a very comfortable spot for your...
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    South Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, Sleeps 8
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    About this property
    Friday to Friday Rental This cottage is converted out of an a barn built in 1792. The upstairs bedroom has a full bed and the downstairs bedroom has a day bed (2 twin beds). This cottage is not for everyone. The entrance to the upstairs bedroom is steep and 18' wide. You can see it next to the...
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    South Chatham, Chatham 02659
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Charming, romantic 2 bedroom cottage, kitchenette (no stove), dining living combined, two balconies, some water views. Fire Pit. Across from Stage Harbor. Great beach walking, amazing sunsets, watch fishermen come in. Use of paddle boards. 1 1/2 ml walk into quaint Chatham village. One of Chatham's...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Smoking allowed
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    2018 Rental Rates (Cleaning Fee Included): In-Season: $1,750 per week Off-Season: $1,275 per week Click for More Photos, Map, and Availability Calendar Recently remodeled cottage with central air is close to shopping and restaurants in downtown Chatham, baseball games at Veteran's Field, and...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, Sleeps 6
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    About this property
    Come stay in this lovely, light, bright and open 2+ bedroom, 2.5 bath home with a deck overlooking a very private backyard with enclosed outdoor shower and charcoal grill. This rental is convenient to shopping, restaurants and beaches. Schoolhouse Pond is less than a mile away and Pleasant...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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