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Compare 117 Vacation Homes in Winchester with updated reviews, rates, and availability.

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (25)
"Easy stay, good location for us. Would stay again. "
The price is AED 474
AED 792 total
includes taxes & fees
8 Jun - 9 Jun
Lovely 2nd Floor Apartment

Family Friendly Hilltop House In Putney Vermont

9.6 out of 10, Exceptional, (54)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is AED 716
AED 1,251 total
includes taxes & fees
1 Jun - 2 Jun
Family Friendly Hilltop House In Putney Vermont

Downtown Hot Tub Escape

9.4 out of 10, Exceptional, (11)
"Brought my parents and my Brother to this rental - It was a nice place."
The price is AED 731
AED 1,343 total
includes taxes & fees
1 Jun - 2 Jun
Downtown Hot Tub Escape

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

10.0 out of 10, Exceptional, (73)
"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

Story Book Lake Front Chateau with Private Beach!

10.0 out of 10, Exceptional, (6)
"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, (4)
"In town for funeral, the place was great. Very roomy and comfy."
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

Quiet private pond getaway

9.4 out of 10, Exceptional, (9)
"We really enjoyed our time at the lake house! The deck and fire pit was fun and everything was very nicely decorated and had enough supplies to make it very easy and a quiet peaceful setting!"
Quiet private pond getaway

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!

Spacious 4-bedroom Pet Friendly Home Near Lakes and Hiking

10.0 out of 10, Exceptional, (1)
"We had a great experience at Erika’s place. The house was great. Spacious & cozy at the same time. Plenty of amenities to keep the kids entertained from the theater in the basement to card games, fussball, darts, backyard, and firepit,for roasting marshmallows. We hiked at Molly Stark, went to the reservoir, & skied at Mt. Snow all in under 20 min away. We had a good time, it was a perfect getaway for our spring break. "
Spacious 4-bedroom Pet Friendly Home Near Lakes and Hiking

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (8)
"Great place! Location was ideal, close to everything. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

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

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

8.4 out of 10, Very Good, (27)
"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, (15)
"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

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

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (15)
"We enjoyed our stay. AWD is a must for the driveway. The number of security cameras around the property is uncomfortable."
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Spectacular Mountain views with all the amentities nearby

9.8 out of 10, Exceptional, (53)
"Beautifully decorated retreat in the treetops."
Spectacular Mountain views with all the amentities nearby

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

9.8 out of 10, Exceptional, (16)
"Very nice house and property! "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby

Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking

10.0 out of 10, Exceptional, (30)
"The house was so well stocked and very child friendly. So many personal touches that made us feel at home and comfortable. Would definitely stay again!"
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking

Inviting mountain view home with game room, balcony & W/D

8.8 out of 10, Excellent, (8)
"This house was perfect in every way for our family gathering. The location is remote enough that you feel like you are getting away, but very close to shops, restaurants etc. The house is very well equipped as well- kitchen has everything you would ever need for cooking and entertaining. There were also many games and a Bluetooth speaker available. We thoroughly enjoyed our time here and are even already talking about booking it again next year."
Inviting mountain view home with game room, balcony & W/D
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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