Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Winchester vacation rentals

Exterior

Cozy & Bright Guest Suite

Cozy & Bright Guest Suite
Peterborough
The price is ￥12,578
￥29,853 total
includes taxes & fees
Feb 10 - Feb 11
Cozy & Bright Guest Suite
Smart TV, fireplace, printers

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (23 reviews)
"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."
United States
Nicole B.
The price is ￥24,055
￥52,029 total
includes taxes & fees
Feb 10 - Feb 11
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Private kitchen

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The Studio with a View. Bring your dog, too!
Exterior detail

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Peterborough
9.8 out of 10, Exceptional, (31 reviews)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is ￥9,197
￥21,919 total
includes taxes & fees
Feb 10 - Feb 11
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (48 reviews)
"Very cute apartment, clean and nice furnishings, bed was very comfortable."
United States
Matthew H.
The price is ￥18,253
￥31,629 total
includes taxes & fees
Feb 10 - Feb 11
Lovely 2nd Floor Apartment
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
The price is ￥13,364
￥32,512 total
includes taxes & fees
Feb 28 - Mar 1
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Exterior

Finnish Cabin with Sauna on Lake Monomonac

Finnish Cabin with Sauna on Lake Monomonac
Rindge
10.0 out of 10, Exceptional, (11 reviews)
"Amazing place. We really enjoyed our brief stay. Great host. "
United States
Gary S.
The price is ￥23,748
￥46,237 total
includes taxes & fees
Feb 10 - Feb 11
Finnish Cabin with Sauna on Lake Monomonac
Property grounds

Grey Cabin with Sauna on Lake Monomonac

Grey Cabin with Sauna on Lake Monomonac
Rindge
7.6 out of 10, Good, (4 reviews)
"Great location host was on it.anything u needed he was there.no ac was the only thing.but it was unusally hot.i would go again"
United States
Brian
The price is ￥26,735
￥52,378 total
includes taxes & fees
Feb 18 - Feb 19
Grey Cabin with Sauna on Lake Monomonac
Exterior

Beautiful Adirondack Cabin with Sauna on Lake Monomonac

Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Rindge
9.8 out of 10, Exceptional, (25 reviews)
"This is a great property, and Jim is a wonderful host. He accommodated all our requests for sauna use and provided helpful tips about the area. We hope to return again one day!"
United States
Leigh C.
The price is ￥29,722
￥58,349 total
includes taxes & fees
Feb 10 - Feb 11
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is ￥27,514
￥34,194 total
includes taxes & fees
Feb 10 - Feb 11
Vikings Villages Resort - Double Bed Room
Outdoor spa tub

Modern Downtown 12ppl Hot Tub Fire Pit Games

Modern Downtown 12ppl Hot Tub Fire Pit Games
Keene
9.6 out of 10, Exceptional, (22 reviews)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is ￥23,583
￥47,935 total
includes taxes & fees
Feb 26 - Feb 27
Modern Downtown 12ppl Hot Tub Fire Pit Games
Living area

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
10.0 out of 10, Exceptional, (1 review)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
United States
Grant D.
The price is ￥20,783
￥63,954 total
includes taxes & fees
Feb 11 - Feb 12
Stunning Glass House nestled in the Vermont wilderness!
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥23,621
￥73,197 total
includes taxes & fees
Mar 2 - Mar 3
Chalet Mount Snow/Stratton Skiing/hiking
Property grounds

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
Whitingham
10.0 out of 10, Exceptional, (1 review)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is ￥22,011
￥48,424 total
includes taxes & fees
Feb 10 - Feb 11
Lake Whitingham & Mount Snow Area Village Apartment
WiFi, bed sheets

Spacious lakeside 4-bedroom house in beautiful Ashburnham

Spacious lakeside 4-bedroom house in beautiful Ashburnham
Ashburnham
The price is ￥31,444
￥56,335 total
includes taxes & fees
Feb 11 - Feb 12
Spacious lakeside 4-bedroom house in beautiful Ashburnham
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is ￥32,175
￥39,687 total
includes taxes & fees
Feb 10 - Feb 11
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Terrace/patio

Terrific 3-bedroom unit in charming Leverett with AC

Terrific 3-bedroom unit in charming Leverett with AC
Leverett
10.0 out of 10, Exceptional, (1 review)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
The price is ￥35,375
￥74,287 total
includes taxes & fees
Feb 10 - Feb 11
Terrific 3-bedroom unit in charming Leverett with AC
Exterior

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
West Dover
10.0 out of 10, Exceptional, (23 reviews)
"Wonderful time..the home was very spacious and comfortable..great location!"
United States
Ellen P.
The price is ￥45,704
￥118,267 total
includes taxes & fees
Feb 10 - Feb 11
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
Exterior

2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is ￥14,464
￥28,273 total
includes taxes & fees
Mar 3 - Mar 4
2 Twin beds on 1st floor with En-suite bathroom.
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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Top Winchester Hotel Reviews

Four Columns Inn

Four Columns Inn

10/10 Excellent
"We stayed in the John Fane room which is in the main building. It is cute as a button. Perfect for couples. "
Kathryn Mae 2-night trip
Posted 2 days ago
Four Columns Inn

Find out more about Winchester

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Frequently asked questions

Can I find a vacation rental in Winchester?

Yes, we give you a choice of vacation rentals in Winchester close to Rhododendron State Park, or you can select a secluded option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Winchester. Make sure you have time to check out the forests and waterfront during your trip.

What's the top vacation rental that Winchester has to offer?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This vacation home rental outside of Winchester is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

What’s there to see and do in Winchester?

Barden State Wildlife Management Area and Ashuelot River are a couple of lovely local spots to get outside and enjoy nature. While here, New England Sweetwater Farm & Distillery and Bennett Gorge are other places worth a visit.

What’s a vacation rental in Winchester like?

Vacation rentals are private properties you can stay in for a long or short time in Winchester. Vacation rentals offer amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitized environment, vacation rentals can provide a sense of safety away from public hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip.