Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Winchester vacation rentals

Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (50 reviews)
"Very clean, cozy and lots of nice plants! "
United States
Mary
The price is ￥18,505
￥32,066 total
includes taxes & fees
Mar 29 - Mar 30
Lovely 2nd Floor Apartment
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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 ￥28,690
￥49,980 total
includes taxes & fees
Mar 28 - Mar 29
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Fridge, microwave, oven, stovetop

Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
9.8 out of 10, Exceptional, (48 reviews)
"Great house for family gatherings "
United Kingdom
John Paul B.
The price is ￥45,147
￥101,526 total
includes taxes & fees
Mar 29 - Mar 30
Spacious 5BR w/ Hot Tub & Games
House (4 Bedrooms) | Interior

Outdoor Adventure Haven 14 Mi to Mount Snow Skiing

Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
3.0 star property
Newfane
The price is ￥35,705
￥91,288 total
includes taxes & fees
Mar 29 - Mar 30
Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
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 ￥26,538
￥56,637 total
includes taxes & fees
Mar 29 - Mar 30
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Interior

Enjoy your stay in an antique home in an antique toy museum!

Enjoy your stay in an antique home in an antique toy museum!
Winchendon
9.4 out of 10, Exceptional, (8 reviews)
"What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!"
United States
Katja Z.
The price is ￥62,959
￥82,385 total
includes taxes & fees
Mar 27 - Mar 28
Enjoy your stay in an antique home in an antique toy museum!
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 ￥22,315
￥48,914 total
includes taxes & fees
Mar 27 - Mar 28
Lake Whitingham & Mount Snow Area Village Apartment
Exterior

2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is ￥89,131
￥129,567 total
includes taxes & fees
Mar 29 - Mar 30
2 Cabins & Sauna on Lake Monomonac
Exterior

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is ￥24,745
￥46,868 total
includes taxes & fees
Mar 29 - Mar 30
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Living area

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.8 out of 10, Excellent, (3 reviews)
"The was an excellent experience all around! The place is immaculate and exactly as described, stylish and functional for our group of 8. Appreciated the fireplace, flat screens and PacMan. Check in/out instructions clear and communication w owner quick. The location was convenient for skiing Mt Snow. Jax on Tap a great spot right below for dinner and fun- our crew played shuffleboard and pool. Food was delicious! "
United States
Claudia M.
The price is ￥58,018
￥102,826 total
includes taxes & fees
Mar 27 - Mar 28
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Terrace/patio

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (51 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is ￥46,478
￥95,393 total
includes taxes & fees
Mar 31 - Apr 1
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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 ￥22,825
￥41,195 total
includes taxes & fees
Mar 27 - Mar 28
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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, (33 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 ￥11,476
￥24,557 total
includes taxes & fees
Mar 29 - Mar 30
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Fridge, microwave, oven, stovetop

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Dublin
10.0 out of 10, Exceptional, (26 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is ￥66,944
￥114,122 total
includes taxes & fees
Mar 30 - Mar 31
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
Exterior

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is ￥21,518
￥40,881 total
includes taxes & fees
Mar 31 - Apr 1
Wellness Getaway with a Personal Sauna, and Private River Beach!
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 price is ￥21,039
￥42,129 total
includes taxes & fees
Apr 6 - Apr 7
The Studio with a View. Bring your dog, too!
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 ￥32,850
￥40,485 total
includes taxes & fees
Mar 29 - Mar 30
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior

3 Cabins/Houses and Sauna on Lake Monomonac near Mt. Monadnock

3 Cabins/Houses and Sauna on Lake Monomonac near Mt. Monadnock
Rindge
The price is ￥114,633
￥178,335 total
includes taxes & fees
Mar 29 - Mar 30
3 Cabins/Houses and Sauna on Lake Monomonac near Mt. Monadnock
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is ￥35,863
￥44,264 total
includes taxes & fees
Mar 29 - Mar 30
Vikings Villages Resort - Double Bed Room
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (12 reviews)
"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "
United States
Rebecca
The price is ￥26,180
￥41,550 total
includes taxes & fees
Mar 29 - Mar 30
Cabin & Sauna on Lake Monomonac near Mt. 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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Top Winchester Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"Clean, quiet, felt safe, staff was friendly, reasonably priced."
Beth 3-night trip
Posted 1 day ago
The Putney 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?

Lovely 2nd Floor Apartment: This vacation home rental outside of Winchester offers a garden, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in Winchester?

Cass Pond and Rhododendron State Park are a couple of lovely local spots to get outside and enjoy nature. While here, New England Sweetwater Farm & Distillery and Pisgah State Park 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.