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Vacation Homes in Winchester

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is AED 374
AED 680 total
includes taxes & fees
17 Jul - 18 Jul
Lovely 2nd Floor Apartment

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (78)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Timeless Red Sox Retreat w/ Scenic Mountain Views!

10.0 out of 10, Exceptional, (22)
"Beautiful property "
Timeless Red Sox Retreat w/ Scenic Mountain Views!

Story Book Lake Front Chateau with Private Beach!

10.0 out of 10, Exceptional, (8)
"We loved staying here! The property was sparkling clean and very well stocked with everything you need. Comfortable beds and space. The view was beautiful and the privacy and yard created great memories for our family. Thank you sharing your beautiful house with us!"
Story Book Lake Front Chateau with Private Beach!

Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

10.0 out of 10, Exceptional, (5)
"In town for funeral, the place was great. Very roomy and comfy."
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (14)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is AED 1,543
AED 2,339 total
includes taxes & fees
7 Aug - 8 Aug
Downtown Hot Tub Escape

LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!

2.0 star property
9.0 out of 10, Wonderful, (8)
"Needed place to stay in Ashburnham large enough to sleep extended family traveling in for the holidays. Cabin was quaint, rustic and fit all of us. Overall good stay. "
LAKE FRONT: Cozy 4-bedroom lake CAMP with WiFi and an outdoor firepit!

Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

10.0 out of 10, Exceptional, (27)
"Beautiful property with great quality towels, furniture, and amenities. Great views and great location. Would be happy to stay again. "
Shelburne Falls #1 Rated STR. Blue on South. Style design with comfort..

Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

10.0 out of 10, Exceptional, (65)
"There house is large and comfortable. Wayne was very helpful and accommodating. Highly recommend. "
Spacious Estate With Mtn Views! Private Setting, Great Family Home!!

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (103)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11

Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

10.0 out of 10, Exceptional, (1)
"This was such a nice stay. Not only was the house really clean, there were so many little touches. It gave cozy spa vibes. "
The price is AED 551
AED 1,264 total
includes taxes & fees
31 Jul - 1 Aug
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great Views

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (38)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

Modern Waterfront Gem w/ Dock on Lake Monomonac

10.0 out of 10, Exceptional, (4)
"Beautiful cottage on the lake. Everything seams new and spotless. Would definitely stay again."
Modern Waterfront Gem w/ Dock on Lake Monomonac

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is AED 716
AED 1,251 total
includes taxes & fees
16 Aug - 17 Aug
Family Friendly Hilltop House In Putney Vermont

Bright three-level home with water views, jetted tub, firepit, and pool table

8.4 out of 10, Very Good, (29)
"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"
Bright three-level home with water views, jetted tub, firepit, and pool table

Rustic, dog-friendly escape with private pool, sweeping views, & W/D

9.4 out of 10, Exceptional, (16)
"The house was great and offered amazing views of the VT mountains! Definitely recommend it and will be back!"
Rustic, dog-friendly escape with private pool, sweeping views, & W/D

Four Season Woodsy Retreat with Private Pool. Skiing, Hiking, Kayaking

Four Season Woodsy Retreat with Private Pool. Skiing, Hiking, Kayaking

Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

9.8 out of 10, Exceptional, (16)
"Wonderful home. Owners are very helpful & hands on. Completely enjoyed the property. "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

Spacious Estate w/ Courtyard: 2 Miles to Downtown!

10.0 out of 10, Exceptional, (5)
"Many, many thanks to Janet, a super host who went above and beyond to ensure that our stay was great in every way. The home is gorgeous; every room is tastefully decorated and very comfortable. Kitchen is very well-equipped and easily handled preparing dinner for 20. Short trip to center of Keene, and lots of parking at the house. Beautiful lawns and gardens around the home; there were still some blooms in late September! Many fascinating features in the home, including beautiful mosaic...
Spacious Estate w/ Courtyard: 2 Miles to Downtown!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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