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Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

Vacation Rentals in Winchester

Exterior
Tiny house on the Ashuelot river family and pet friendly

Tiny house on the Ashuelot river family and pet friendly

Swanzey
The price is ￥9,205
￥13,317 total
includes taxes & fees
Nov 10 - Nov 11
Tiny house on the Ashuelot river family and pet friendly
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!

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

2.0 star property
Newfane
10.0 out of 10, Exceptional, (1)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is ￥20,712
￥39,006 total
includes taxes & fees
Nov 17 - Nov 18
Wellness Getaway with a Personal Sauna, and Private River Beach!
Exterior detail
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Greenfield
10.0 out of 10, Exceptional, (1)
"We had an amazing stay! The property was spotless and comfortable. We felt right at home and can’t wait to stay here again! "
United States
Garth P.
The price is ￥9,942
￥31,669 total
includes taxes & fees
Nov 10 - Nov 11
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Fridge, microwave, oven, stovetop
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, (28)
"My stay was what I wanted – quiet and time to study and pray. The town has many beautiful brick buildings and quaint shops for shopping. I thoroughly enjoyed my stay."
United States
Betty D.
The price is ￥11,737
￥24,386 total
includes taxes & fees
Nov 11 - Nov 12
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Fitzwilliam
10.0 out of 10, Exceptional, (13)
"Our two night stay was great. Loved how close it was to the bike path and the fire pit in the back. Clare was very responsive!"
United States
Camila G.
The price is ￥19,193
￥31,645 total
includes taxes & fees
Nov 10 - Nov 11
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking

East Dover
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥17,969
￥66,899 total
includes taxes & fees
Nov 20 - Nov 21
Mountain Chalet mins from Mt Snow Skiing/hiking
Interior
Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Greenfield
10.0 out of 10, Exceptional, (43)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
United States
Shanyn
The price is ￥17,812
￥30,865 total
includes taxes & fees
Nov 10 - Nov 11
Lovely 2nd Floor Apartment
Property grounds
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)
"Catherine contacted me immediately that the studio I had rented was not available but that we could have the adjacent house instead. She moved heaven and earth to make sure we had a king bed ( which is what we wanted). She was very attentive and accommodating. "
United States
Wendy C.
The price is ￥13,041
￥31,553 total
includes taxes & fees
Nov 30 - Dec 1
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Terrace/patio
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, (20)
"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 ￥26,235
￥55,598 total
includes taxes & fees
Nov 10 - Nov 11
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Property grounds
Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment

2.0 star property
Whitingham
10.0 out of 10, Exceptional, (1)
"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 ￥21,479
￥46,738 total
includes taxes & fees
Nov 10 - Nov 11
Lake Whitingham & Mount Snow Area Village Apartment
Interior
Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!

Guilford
10.0 out of 10, Exceptional, (1)
"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 ￥18,789
￥61,079 total
includes taxes & fees
Nov 11 - Nov 12
Stunning Glass House nestled in the Vermont wilderness!
Exterior
Beautiful Adirondack Cabin with Sauna on Lake Monomonac

Beautiful Adirondack Cabin with Sauna on Lake Monomonac

2.0 star property
Rindge
10.0 out of 10, Exceptional, (24)
"Host was incredibly friendly and accommodating and the cabin was nothing short of beautiful"
United States
Moose C.
The price is ￥33,001
￥54,451 total
includes taxes & fees
Nov 10 - Nov 11
Beautiful Adirondack Cabin with Sauna on Lake Monomonac
Property grounds
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Putney
9.4 out of 10, Exceptional, (56)
"Gorgeous property. Super accommodating hosts. Would love to come back in the summer."
United States
Thomas F.
The price is ￥19,178
￥39,006 total
includes taxes & fees
Nov 10 - Nov 11
Family Friendly Hilltop House In Putney Vermont
Exterior
Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.

Dublin
10.0 out of 10, Exceptional, (5)
"Very nice well kept and a great location to Monadnock Hospital."
United States
Melissa M.
The price is ￥29,273
￥44,594 total
includes taxes & fees
Nov 17 - Nov 18
Cozy Tiny House on Main Street. Fully Renovated.
Property grounds
Grey Cabin with Sauna on Lake Monomonac

Grey Cabin with Sauna on Lake Monomonac

2.0 star property
Rindge
7.6 out of 10, Good, (4)
"Hit the jackpot at this stay .Awesome area with many things to keep busy outside ,hiking all around ,lake for all kind of activities .Jim was a great host filled us in on activities in the area and was a message away for any help u may need .I will be back ."
United States
David S.
The price is ￥30,239
￥51,121 total
includes taxes & fees
Nov 10 - Nov 11
Grey Cabin with Sauna on Lake Monomonac
Outdoor spa tub
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow

Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow

West Dover
10.0 out of 10, Exceptional, (20)
"great space for adults and teenagers. loved the hot tub! "
United States
Jessica M.
The price is ￥27,478
￥93,634 total
includes taxes & fees
Nov 10 - Nov 11
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow
Exterior
Finnish Cabin with Sauna on Lake Monomonac

Finnish Cabin with Sauna on Lake Monomonac

2.0 star property
Rindge
10.0 out of 10, Exceptional, (11)
"This was a very nice cozy cottage, with a nice view of the water. The host was friendly and accommodating. We look forward to staying again."
United States
Cintromix
The price is ￥34,381
￥51,454 total
includes taxes & fees
Nov 10 - Nov 11
Finnish Cabin with Sauna on Lake Monomonac
Fridge, microwave, oven, stovetop
Downtown Hot Tub Escape

Downtown Hot Tub Escape

Keene
9.6 out of 10, Exceptional, (21)
"The house was adorable! Great place for a getaway! We did realize almost all of the cups were dirty so we cleaned a lot our first day there. We also had issues with the hot water. As a group of 8 and only one bathroom we made it work but not having hot water was rough! Oh and blowing the fuse anytime we wanted to coffee! But for an old home it was nice!"
United States
Jacqueline V.
The price is ￥25,951
￥50,630 total
includes taxes & fees
Nov 12 - Nov 13
Downtown Hot Tub Escape
Dining
Couples 2 Bedroom Retreat-Close to Shelburne Falls

Couples 2 Bedroom Retreat-Close to Shelburne Falls

Colrain
10.0 out of 10, Exceptional, (4)
"We had everything we needed for a fun and relaxing family get away. We loved how close it was to great restaurants and activities like rafting, zip lining, and the mountain coaster. The kitchen is fully stocked and everything was clean and well organized.Erica and Casey were great hosts and so helpful in answering any and all of our questions before check in. We will definitely be back! "
United States
Heather B.
The price is ￥26,081
￥57,581 total
includes taxes & fees
Nov 11 - Nov 12
Couples 2 Bedroom Retreat-Close to Shelburne Falls
Exterior
Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room

Guilford
The price is ￥42,191
￥56,424 total
includes taxes & fees
Nov 10 - Nov 11
Vikings Villages Resort - Double Bed Room
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

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

10/10 Excellent
"This place is great. The staff very friendly rooms clean lobby cozy. The breakfast was good with lots of choice and plenty of places to sit. Would definitely recommend "
Bambi 1-night trip
Posted 22 hours ago
Best Western Plus Keene Hotel

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?

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC: This vacation home rental outside of Winchester is located in the mountains and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings. You and your friends and family can relax into your vacation with amenities like a selection of games.

What’s there to see and do in Winchester?

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