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Vacation rentals in Windsor, VT and nearby

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All 33 Rentals in the Windsor Area
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From
$290
Per Night
1 / 29
Windsor
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (12) Make Enquiry

The following rentals are within 25 kilometres of Windsor, Vermont.

From
$290
Per Night
1 / 19
Payment Protection
Reading
4 Bedrooms, 1 Bathroom, Sleeps 8
Details Reviews (5) Make Enquiry
From
$1,797
Per Night
1 / 29
Payment Protection
Reading
15 Bedrooms, 11 Bathrooms, Sleeps 41
Details Reviews (3) Make Enquiry
From
$232
Per Night
1 / 20
Payment Protection
Claremont, NH
4 Bedrooms, 3 Bathrooms, Sleeps 10
Booking
Details Reviews (3) Make Enquiry
Amenities & Details
  • Parking
  • Dishwasher
  • Washer
  • Patio
  • Waterfront
  • Dryer
  • Microwave
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Welcome to North Star House and the Connecticut River Scenic Byway. Located on 700 acres in Cornish and Claremont New Hampshire, North Star House is the result of our year-long top-to-bottom restoration of this 1855 historic home. We’ve retained all of the historic features – slate roof, antique... View all property information
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5 of 5 stars Reviewed 12 October 2014
Bill and Jenny have a beautiful renovated house. The stay was awesome, felt right at home. Loved that they accepted pets because our two Corgis are our family. We went to New...
5 of 5 stars Reviewed 3 October 2014
Not only is North Star House perfect in its appointments (comfy bedrooms, bathrooms you could dance in, and a kitchen of your dreams), it also is perfectly situated on the...
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From
$220
Per Night
1 / 10
Payment Protection
Quechee
4 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Washer
  • TV
  • Linens Provided
  • Dryer
  • Deck
  • Parking
  • Satellite TV
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Our clean and welcoming 4 BR home filled w/ beautiful natural light is perfect for your Vermont Getaway. It features beautiful views, brand new furniture, and modern amenities. Our home is completely ready for you with each bathroom filled with fresh towels, linens, and soap. With four bedrooms it... View all property information
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4 of 5 stars Reviewed 23 November 2014
Justin started out our rental experience with prompt replies to all of our questions and requests. When we got to the house,it was larger than we had expected from the pictures on...
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From
$157
Per Night
1 / 24
Payment Protection
Perkinsville
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (12) Make Enquiry
Amenities & Details
  • DVD Player
  • TV
  • Dishwasher
  • Microwave
  • Patio
  • Dryer
  • Washer
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
High Shelter Farm is a sheep farm offering complete privacy from the road, lovely views of Mount Ascutney, and 5 miles of recreational trails through the 270 acre property. The four-room guest apartment is the 1200 square foot ground floor of our farmhouse. Your hosts live on the upper floors... View all property information
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5 of 5 stars Reviewed 11 March 2014
We could not have asked for more. This place is heavenly, and Grace (the owner), was wonderful. We can hardly wait to visit again; this time for much longer. All you need to...
5 of 5 stars Reviewed 30 September 2013
High Shelter Farm was a fantastic vacation in every way and Grace was wonderful, too! When we arrived Grace had muffins, eggs from her chickens, bread, milk and cider. It was a...
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From
$290
Per Night
1 / 20
Payment Protection
Reading
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Washer
  • Deck
  • Dryer
  • Microwave
  • Fireplace
  • Internet Access
  • Grill
  • Porch
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Nestled in a private hundred-acre valley crisscrossed with trails, a quiet, beautifully situated antique cabin and fully renovated barn overlooking idyllic Vermont meadow, ponds, hills & creek awaits your discovery. Property abuts the world famous Jenne Farm located twenty minutes south of... View all property information
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5 of 5 stars Reviewed 30 June 2014
We were looking for a quiet spot for our family to get away from our crazy day-to-day life, and we found it! The cabin was great - clean, comfortable, well-stocked - and the porch...
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From
$232
Per Night
1 / 9
Payment Protection
Chester
1 Bedroom, 1 Bathroom, Sleeps 3
Details Reviews (1) Make Enquiry
Amenities & Details
  • Refrigerator
  • Dryer
  • TV
  • Deck
  • Porch
  • Washer
  • VCR
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Our charming well appointed private apartment is perfect for anyone looking for a quiet place to rest, relax and recharge in the beautiful Southern Vermont countryside. Situated on rural Popple Dungeon Road between Chester and historic Grafton and close to skiing, Nordic centers, spas, antiquing,... View all property information
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From
$261
Per Night
1 / 3
Payment Protection
Brownsville
Studio, 3 Bathrooms, Sleeps 7
Details Make Enquiry
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
The condominium lies on the West face of historical Ascutney Mt in the small town of Brownsville. The condominium consists of 3 bedrooms, 2 1/2 bathrooms, a small family rec room, living room, and dining area. A very comfy and warm atmosphere with access to a full service sports and fitness center.... View all property information
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From
$145
Per Night
1 / 14
Payment Protection
Newport
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • VCR
  • Microwave
  • Porch
  • Stereo System
  • Internet Access
  • Garden
  • DVD Player
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • x
About this property
Your home away from home while you kick back on a cozy retreat or adventure on the slopes or skimobile, icefish, catch a country auction or spend a day in Montreal, nights at the trendy bars and restaurants in this quaint little town of Newport, 5 miles to the Canadian border, on Lake Memphramegog.... View all property information
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From
$203
Per Night
1 / 31
Payment Protection
Newport, NH
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Deck
  • TV
  • Refrigerator
  • Parking
  • Wi-Fi
  • Microwave
  • Fireplace
  • Stereo System
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Located at the historic estate and summer residence of 2-term New Hampshire Governor Francis P. Murphy, the 'Lodge' is a truly unique space with timeless and upscale accommodations that make this far more than your traditional rental destination. Stepping into the Lodge, you're transported back in... View all property information
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From
$388
Per Night
1 / 32
Payment Protection
Sunapee, NH
3 Bedrooms, 2 Bathrooms, Sleeps 9
Details Make Enquiry
Amenities & Details
  • DVD Player
  • TV
  • Parking
  • Grill
  • Garage
  • Microwave
  • Refrigerator
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
You’ll feel like you’re vacationing inside the pages of DWELL magazine in this brand new three/four bedroom lakefront house designed by a prominent Boston architect. Charming Kezar Lake, dotted with old farmhouses and inns, is a well-kept secret in the area. Old-fashioned Vernondale General Store,... View all property information
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From
$348
Per Night
1 / 10
Payment Protection
Quechee
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Pool
  • Dryer
  • Washer
  • DVD Player
  • Refrigerator
  • Deck
  • Microwave
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This Townhouse is in one of the most recently completed Quechee Lakes communities. Newton Village is part of the Quechee Club, situated in the Ottauquechee River valley, between Dartmouth College, Hanover NH and Woodstock VT, easily accessible from Interstates 89 and 91. The Quechee Club is a... View all property information
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From
$362
Per Night
1 / 16
Payment Protection
Perkinsville
5 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
Details Make Enquiry
Amenities & Details
  • Dryer
  • Garage
  • Washer
  • Patio
  • Refrigerator
  • Fireplace
  • Dishwasher
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Beautiful contemporary mountain home in Vermont sitting in 150 acres of private land. Borders a State Park with beautiful trails and an 80 ft Cascade. 5 Bedrooms, sleeps up to 12. This sprawling home features a large kitchen, separate dining room, spacious living room with stone fireplace and... View all property information
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From
$231
Per Night
1 / 10
Payment Protection
Quechee
8 Bedrooms, 10 Bathrooms, Sleeps 16
Details Make Enquiry
Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
On a vacation, who wants to spend all their time picking-up and cooking for themselves? At The Parker House Inn, we do all that and more for you! Our full service, Pet Friendly Inn boasts eight newly decorated guestrooms, all with private baths, some with Whirlpools Baths or Spa Showers. Queen and... View all property information
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From
$510
Per Night
1 / 10
Payment Protection
Proctorsville
3 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
Details Make Enquiry
Amenities & Details
  • Refrigerator
  • Hot Tub
  • DVD Player
  • Dryer
  • Dishwasher
  • Parking
  • Patio
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Our home is a beautiful 3 bedroom, 2 bath with large family room and sleeps 10. In winter we are 4 minutes to skiing at the fabulous resort of Okemo/Jackson Gore. You ski, board, ice skate, snowmobile, snow shoe, cross country or go to the spa for a day of fun. At our house we have an outdoor hot... View all property information
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From
$151
Per Night
1 / 46
Payment Protection
Sunapee, NH
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Make Enquiry
Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
My 3 season waterfront cabin is appointed with true 'cabin style' charm but with all the modern amenities. The cabin is directly on Perkins Pond and provides amazing views and sunsets. There are 2 large decks, a wharf for sunning, and lighted landscaped pathway. Two kayaks are included to explore... View all property information
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From
$899
Per Night
1 / 35
Payment Protection
Lowell
6 Bedrooms, 5 Bathrooms, Sleeps 16
Details Make Enquiry
Amenities & Details
  • Microwave
  • Pool Table
  • Ceiling Fans
  • Patio
  • TV
  • Refrigerator
  • Garage
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Be one of the first to stay in this newly finished 4000 square foot home, just 12 miles from Jay Peak Resort. In winter Jay Peak offers the most snow and the best glades in the east for skiers and riders of all abilities. ASK ABOUT OUR DISCOUNT SKI LIFT TICKETS!Cross country ski or snowshoe right... View all property information
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From
$638
Per Night
1 / 30
Payment Protection
Chester
6 Bedrooms, 7 Bathrooms, Sleeps 18
Details Make Enquiry
Amenities & Details
  • DVD Player
  • Microwave
  • Refrigerator
  • Porch
  • Terrace
  • Ceiling Fans
  • Satellite TV
  • Fax
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This listing is an option for renting the entire Inn. Individual rooms can be rented as well. Please check our other listings for individual rooms. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the... View all property information
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From
$290
Per Night
1 / 8
Payment Protection
Quechee
2 Bedrooms, 1 Bathroom, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Refrigerator
  • Satellite TV
  • Dishwasher
  • Fireplace
  • Grill
  • Dryer
  • Microwave
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Quechee VT townhouse located on top of the ski hill. This two bed, lofted condo is located close to all Queschee Lakes amenties and is close to Woodstock VT and Hanover NH. View all property information
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From
$161
Per Night
1 / 11
Payment Protection
Chester
1 Bedroom, 1 Bathroom, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Terrace
  • Microwave
  • DVD Player
  • Safe
  • Satellite TV
  • TV
  • Refrigerator
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Overlooking the village green, this bright and spacious room accommodates a family or group of people. Has two queen-sized beds and a love-seat sleeper sofa with a twin bed. Has wall-to-wall carpeting, private bath with shower and air conditioning for hot weather days. Also features a infrared... View all property information
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From
$138
Per Night
1 / 10
Payment Protection
Chester
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • VCR
  • Air Conditioning
  • DVD Player
  • Balcony
  • Porch
  • Terrace
  • TV
  • Highchair
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • x
About this property
The Tower Room in Hugging Bear Inn and Shoppe, a bed 'n breakfast Inn. Cozy and romantic with queen-sized bed, full private bathroom with shower and air-conditioning for hot weather days. A round room (actually hexagonal) in the tower of this Victorian home overlooks the village green. Full Vermont... View all property information
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From
$161
Per Night
1 / 10
Payment Protection
Chester
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • DVD Player
  • Air Conditioning
  • Terrace
  • Refrigerator
  • Balcony
  • Porch
  • VCR
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
A room with calming earth tones. This is a medium sized room with one queen and one full double bed, private bathroom with shower and air-conditioning for hot weather days. This listing is an option for renting an individual room in the Inn. The entire Inn can be rented as well. Please check our... View all property information
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From
$220
Per Night
1 / 20
Payment Protection
Quechee
3 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Patio
  • TV
  • Dryer
  • Parking
  • Washer
  • Refrigerator
  • Dishwasher
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Roomy, comfortable three bedroom plus loft townhouse with views of the Vermont hills, within short walking distance of Quechee village. Two and a half baths, full kitchen, laundry, back patio and just up the hill from a great playground for kids. A wonderful place to spend a summer vacation! Fully... View all property information
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From
$232
Per Night
1 / 10
Payment Protection
Chester
3 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • DVD Player
  • Ceiling Fans
  • Parking
  • Dishwasher
  • Microwave
  • Washer
  • Refrigerator
  • Playground
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The perfect Vermont location. This log cabin sits directly above the Williams River with spectacular river and mountain views west and south. Sit on the deck and listen to the rapids rushing below. Go fishing for brook trout on the Williams River directly on the property. The property has one of... View all property information
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From
$157
Per Night
1 / 9
Payment Protection
Newport, NH
3 Bedrooms, 1 Bathroom, Sleeps 7
Details Reviews (1) Make Enquiry
Amenities & Details
  • Microwave
  • Safe
  • Grill
  • Ceiling Fans
  • TV
  • DVD Player
  • VCR
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Located on a quiet, pristine New Hampshire lake, this home and scenic surroundings provide a haven of rest for your vacation. Our private sandy beach sits on 510 feet of shoreline and invites you to enjoy carefree sunbathing and swimming in a safe, beautiful setting. Shade trees on the grounds... View all property information
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From
$754
Per Night
1 / 17
Payment Protection
Perkinsville
5 Bedrooms, 2 Bathrooms, Sleeps 12
Details Reviews (4) Make Enquiry
Amenities & Details
  • Hot Tub
  • DVD Player
  • TV
  • Patio
  • Fireplace
  • Grill
  • Microwave
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Secluded mountain retreat located on 83 acres with private mountain and pond. Originally built in 1910 as a gentleman's hunting lodge, this 'Arts & Craft' style home is a wonderful year round retreat. Newly renovated interior, new pictures to come upon completion in July 2013!!! This home... View all property information
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From
$348
Per Night
1 / 12
Quechee
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • DVD Player
  • Microwave
  • Stereo System
  • Refrigerator
  • Deck
  • Washer
  • Fireplace
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Beautiful 3 bedroom condominium on The Ridge at Quechee Lakes. Perfect for golfers, tennis players and skiers who want easy access to courses, courts and mountains. Master bedroom located on second floor (street level) with kitchen, living and dining rooms. Deck, located off the dining room... View all property information
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From
$203
Per Night
1 / 21
Chester
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Refrigerator
  • Dryer
  • Microwave
  • Fireplace
  • Garage
  • Washer
  • Dishwasher
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Charming Antique Colonial/Farmhouse with 5 bedrooms, 3 full baths, two living rooms, huge dining room. Also has a great covered outdoor space (see pics, it's hard to describe), a two-acre field, frontage on the middle branch Williams River, large hay barn, covered two-car parking (and plenty of... View all property information
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From
$116
Per Night
1 / 16
Sunapee, NH
3 Bedrooms, 4 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Garage
  • Microwave
  • Refrigerator
  • Washer
  • Dryer
  • Fireplace
  • DVD Player
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This is a MONTHLY rental only. There is a 3 MONTH minimum requirement. Please see the rates section below for more details. Spacious fully furnished 3,000 sf luxurious condo in a highly desirable condominium community four miles from Mount Sunapee Ski Resort with Fall, Winter, and Spring Lake... View all property information
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From
$290
Per Night
1 / 17
Chester
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Dryer
  • Patio
  • Microwave
  • Fireplace
  • Parking
  • DVD Player
  • Garage
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Classic colonial; Large white 2-story 1819 farmhouse w 5 BR, 3 B, rustic family room w/ fireplace; 2 parlors w fireplace, large eat-in kitchen, DR office w INternet WiFi; cable; phone; BR w fireplace; huge red barn w deck and hottub; lovely small river in back; beautifully furnished w period... View all property information
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From
$212
Per Night
1 / 10
Brownsville
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Washer
  • Microwave
  • Dishwasher
  • Patio
  • Dryer
  • Satellite TV
  • Terrace
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
A Wonderful House in Brownsville, Vermont 1/4 mi to Ascutney Mountain Resort. 12 miles to Woodstock, VT 30 minutes to Mount Okemo. 4 hours to Manhattan via Merrit Pkwy and I-91 3 hours to Boston The perfect vacation spot for skiing, leaf-peeping, or just kicking back. 24 acres of privacy,... View all property information
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From
$1,633
Per Week
1 / 24
Cavendish
5 Bedrooms, 3 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Grill
  • Horse Riding Nearby
  • Fishing Nearby
  • There Is A Golf...
  • There Are Tennis...
  • Secure Parking
  • Central Heating
  • Towels Provided
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Arranged over 3 floors this is a traditionally constructed log cabin approximately 20 years old set in 4.5 acres of woodland. The building is constructed from 15” thick logs built around a breeze block basement construction and features a main house with porch, deck, adjacent small garage designed... View all property information
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