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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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

Cozy Home Near Downtown, Shops, and Restaurants.
Exterior

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
12 May - 13 May
Cozy Home Near Downtown, Shops, and Restaurants.
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (50)
"Great location, communicative and welcoming hosts, and great amenities. We loved grilling and using the firepit. The surrounding area is great to walk around in. Easy drive from here to Mt Snow."
The Jelly Mill-A River Retreat
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Property grounds

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

10.0 out of 10, Exceptional, (73)
"Very spacious and comfortable. Biggest selling point was its proximity to family in the area."
1810 Brook Side Mill/House / EV Level 2 Charging on Site
GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"The property is very large. Lots of sleeping area. Many activities within the rental to keep everyone off all ages busy, kept finding new things in nooks and crannies. Lots of property got our dog to run. "
GAMERS HAVEN, River Wine Inn!
Family Friendly Hilltop House In Putney Vermont
Exterior

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 1,251 total
includes taxes & fees
10 May - 11 May
Family Friendly Hilltop House In Putney Vermont
Bright three-level home with water views, jetted tub, firepit, and pool table
Fridge, microwave, oven, stovetop

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

8.4 out of 10, Very Good, (27)
"Awesome Cabin, private and peaceful location."
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
Fridge, microwave, oven, stovetop

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
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (21)
"Easy stay, good location for us. Would stay again. "
The price is AED 474
AED 808 total
includes taxes & fees
18 May - 19 May
Lovely 2nd Floor Apartment
Beautiful Lakefront home - perfect getaway for every season!
Miscellaneous

Beautiful Lakefront home - perfect getaway for every season!

10.0 out of 10, Exceptional, (4)
"We had an incredible stay at the lake house. Michelle and Patrick were absolutely wonderful to work with and very responsive throughout our stay. The home is beautiful. Waking up to the lake each morning was such a treat. We definitely hope to visit again!"
Beautiful Lakefront home - perfect getaway for every season!
Hilltop Home with Great Views
Interior

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
TV

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
Fridge, coffee/tea maker, toaster, cookware/dishes/utensils

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
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking
Smart TV, fireplace, foosball, books

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

10.0 out of 10, Exceptional, (30)
"Lovely home with everything you need. Enjoyed yard and the game room. Perfect place for our family ski gathering! Hope to stay here again next year"
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking
Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!
Fridge, microwave, oven, stovetop

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

8.0 out of 10, Very Good, (1)
"The inside of these cabins was exceptionally clean and quaint. We loved the upstairs master bedroom loft! One of our guests needed to use the chair lift on the stairs, and it worked perfectly. The two second bedrooms were nicely equipped and pleasantly decorated. The kitchen had new appliances with a coffee bar. The view of the lake was stunning from multiple views. There were many activities available to take advantage of the outdoor spaces (boats, fire pit, grill, seating, etc.). We really...
Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!
Beautiful, private log cabin with huge, relaxing screened porch
Outdoor dining

Beautiful, private log cabin with huge, relaxing screened porch

10.0 out of 10, Exceptional, (35)
"The cabin was perfect for me and my extended family. It was clean comfortable and had everything we needed for a great stay."
Beautiful, private log cabin with huge, relaxing screened porch
Waterfont log home nestled in the pines
Outdoor dining

Waterfont log home nestled in the pines

10.0 out of 10, Exceptional, (52)
"Second time staying at this property ! Very relaxing, beds super comfortable. Would highly recommend."
Waterfont log home nestled in the pines
Charming Private Cabin w/ Full Kitchen & High-Speed WiFi - Near Mountain
Exterior

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

9.2 out of 10, Wonderful, (23)
"We had a great little getaway for our anniversary and this place was perfect for my husband and I. It’s cozy and private. Would definitely stay again."
Charming Private Cabin w/ Full Kitchen & High-Speed WiFi - Near Mountain
Mount Snow Post and Beam House
Fridge, oven, stovetop, dishwasher

Mount Snow Post and Beam House

10.0 out of 10, Exceptional, (38)
"We had a great weekend, the place was as decribed."
Mount Snow Post and Beam House
River House
Outdoor dining

River House

2.0 star property
10.0 out of 10, Exceptional, (8)
"This place was a great place for my family. They greatly enjoyed the pool table, ping pong table, and river access."
River House
Nestled on the edge of the woods near Mount Monadnock
Fridge, microwave, oven, stovetop

Nestled on the edge of the woods near Mount Monadnock

9.4 out of 10, Exceptional, (6)
"Very nice stay at railtrail retreat."
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

Story Book Lake Front Chateau with Private Beach!
Miscellaneous

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!
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (21)
"Easy stay, good location for us. Would stay again. "
The price is AED 474
AED 808 total
includes taxes & fees
18 May - 19 May
Lovely 2nd Floor Apartment
GAMERS HAVEN, River Wine Inn!
Game room

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"The property is very large. Lots of sleeping area. Many activities within the rental to keep everyone off all ages busy, kept finding new things in nooks and crannies. Lots of property got our dog to run. "
GAMERS HAVEN, River Wine Inn!
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.