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Compare 112 Vacation Homes in Winchester with updated reviews, rates, and availability.

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (3)
"Online info was accurate. Nice spot to rent with family."
The price is AED 1,300
AED 2,152 total
includes taxes & fees
15 Apr - 16 Apr
Cozy Home Near Downtown, Shops, and Restaurants.

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (47)
"Was exactly as described. Had everything we needed and more. Only thing we had hoped for that wasn’t there was some olive oil, so bring your own if you want to cook. Not quite as remote as we were anticipating, but in a good way . Was still very rural, and we were grateful for the 4wheel drive vehicle we rented. Perfect, majestic, natural location for our family retreat."
The Jelly Mill-A River Retreat

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

10.0 out of 10, Exceptional, (71)
"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

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great place with an elite game room. "
GAMERS HAVEN, River Wine Inn!

Family Friendly Hilltop House In Putney Vermont

9.6 out of 10, Exceptional, (54)
"We were caught in the winter storm, and the host was so kind in helping us navigate our car situation. Our kids had such a great time playing in the snow, exploring the books and games they had. "
The price is AED 716
AED 1,242 total
includes taxes & fees
15 Apr - 16 Apr
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, (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

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

7.0 out of 10, Good, (15)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (19)
"Clean, comfortable and quiet. All necessities for kitchen provided. "
The price is AED 400
AED 714 total
includes taxes & fees
15 Apr - 16 Apr
Lovely 2nd Floor Apartment

Beautiful Lakefront home - perfect getaway for every season!

10.0 out of 10, Exceptional, (4)
"We enjoyed our stay at the house. It was clean and the beds were comfortable. The kitchen had all the basics. One thing of note: there is only a countertop toaster oven, not a full size oven. There is a gas cooktop as well. If you plan to cook while there, that will be an important detail. This house has a great view from the living room. We stayed during some very hot days - approaching 90 degrees. There was no air conditioning in the house, but it was still quite comfortable. There seems to be...
Beautiful Lakefront home - perfect getaway for every season!

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

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

9.4 out of 10, Exceptional, (15)
"We had a fun time enjoying the view and playing board games plus outdoor pursuits. Thanks for sharing your home."
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, (2)
"We couldn’t have had a better experience! Such a beautiful cottage—immaculate, gorgeous decor, spectacular deck w/exquisite lake view, super-cozy beds, outstanding communication with hosts! We actually had local plans canceled due to a late March “wintry” ice storm, but couldn’t imagine a better place to hunker down! Hope to return! "
Modern Waterfront Gem w/ Dock on Lake Monomonac

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

10.0 out of 10, Exceptional, (30)
"Everything about this house was wonderful. Clearly an old, well loved house with lots of thoughtful touches and something for everyone. Toys for the kids! Magazines for the adults! A working fireplace for achy grandpa bones! The kitchen is very complete and has everything you need to make a meal. The bedding is super comfortable and the quilts are soft and cloud like. Couldn’t recommend more highly!"
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!

Beautiful, private log cabin with huge, relaxing screened porch

10.0 out of 10, Exceptional, (35)
"The property is exactly as stated in the listing. The host is extremely responsive and great at communicating. The beds were very comfortable and plenty of space for 6 adults. The kitchen was well stocked as well as the wood pile for the stove. Nothing but the best for the property and host. Thank you, Beth!"
Beautiful, private log cabin with huge, relaxing screened porch

Waterfont log home nestled in the pines

10.0 out of 10, Exceptional, (52)
"Anther fantastic time at this beautiful location. Owner is always so geeat to work work "
Waterfont log home nestled in the pines

Charming Private Cabin w/ Full Kitchen & High-Speed WiFi - Near Mountain

9.2 out of 10, Wonderful, (23)
"Clean, well located cabin. Perfect for a family. "
Charming Private Cabin w/ Full Kitchen & High-Speed WiFi - Near Mountain

Mount Snow Post and Beam House

10.0 out of 10, Exceptional, (38)
"Doug’s house is gorgeous and he was very communicative and helpful the entirety of our stay! Special thanks to Ryan for making sure we got out following a massive snow storm"
Mount Snow Post and Beam House

River House

2.0 star property
10.0 out of 10, Exceptional, (8)
"Me and a few friends stayed at the River House during a long weekend during the Winter. The house itself was very nice and had many amenities.The location is good for some of the ski resorts in lower Vermont. However there was a rather large snow storm and due to the half hour 40 minute drive to the mountain we were not able to go because of the roads. This was no fault of the owners obviously but if you want to guarantee getting to the mountain maybe pick a place closer and have access to a car...
River House

Nestled on the edge of the woods near Mount Monadnock

9.4 out of 10, Exceptional, (6)
"House is comfortable and well stocked."
Nestled on the edge of the woods near Mount Monadnock
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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Other property types in Winchester

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"Great place with an elite game room. "
GAMERS HAVEN, River Wine Inn!

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (47)
"Was exactly as described. Had everything we needed and more. Only thing we had hoped for that wasn’t there was some olive oil, so bring your own if you want to cook. Not quite as remote as we were anticipating, but in a good way . Was still very rural, and we were grateful for the 4wheel drive vehicle we rented. Perfect, majestic, natural location for our family retreat."
The Jelly Mill-A River Retreat

Riverfront 2 Bedroom Unit 2

9.6 out of 10, Exceptional, (17)
"Overall, not bad. The host seems thoughtful about what the leave for you to use, but the apartment and exterior could use some TLC"
Riverfront 2 Bedroom Unit 2
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.