A snow-covered town with a river running through it, surrounded by mountains and trees.

Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Winchester vacation rentals

Outdoor dining

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is ￥8,896
￥13,163 total
includes taxes & fees
Jul 1 - Jul 2
2 private mountain RV pads for rent. Full hook ups
Terrace/patio

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (14 reviews)
"Stacy and her husband were very communicative and accommodating. We had everything we needed in the yurt and they provided us with some extra supplies as well. Would definitely stay again!"
United States
Gina M.
The price is ￥18,946
￥30,396 total
includes taxes & fees
Jul 1 - Jul 2
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
House (3 Bedrooms) | Interior

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (58 reviews)
"Very clean and cozy apartment. "
United States
Kim G.
The price is ￥18,800
￥32,758 total
includes taxes & fees
Jul 13 - Jul 14
Lovely 2nd Floor Apartment
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, (39 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is ￥20,241
￥34,261 total
includes taxes & fees
Jul 22 - Jul 23
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Exterior

Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.8 out of 10, Exceptional, (6 reviews)
"Nice place"
United States
Tom
The price is ￥32,898
￥41,985 total
includes taxes & fees
Jul 8 - Jul 9
Light-filled treetop apartment close to downtown Greenfield and Highland Park
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 ￥54,992
￥77,568 total
includes taxes & fees
Jul 1 - Jul 2
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (46 reviews)
"The property was beautiful and it truly felt like an escape. I"
United States
Kristina M.
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
9.8 out of 10, Exceptional, (26 reviews)
"Host was incredibly friendly and accommodating and the cabin was nothing short of beautiful"
United States
Moose C.
The price is ￥72,176
￥100,073 total
includes taxes & fees
Jul 6 - Jul 7
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Property grounds

John's Mountain Hideaway

John's Mountain Hideaway
Jaffrey
10.0 out of 10, Exceptional, (1 review)
"Everything we needed"
United States
Lori S.
The price is ￥46,581
￥86,691 total
includes taxes & fees
Jul 8 - Jul 9
John's Mountain Hideaway
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (61 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is ￥28,968
￥52,732 total
includes taxes & fees
Jul 6 - Jul 7
Family Friendly Hilltop House In Putney Vermont
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
9.6 out of 10, Exceptional, (8 reviews)
"We had a great"
United States
Meredith B.
The price is ￥18,924
￥44,624 total
includes taxes & fees
Jul 8 - Jul 9
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
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)
"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 ￥54,992
￥79,674 total
includes taxes & fees
Jul 1 - Jul 2
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is ￥26,202
￥49,140 total
includes taxes & fees
Jul 6 - Jul 7
Rose wisteria 4 guests 2 bedrooms-full+queen beds
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
9.6 out of 10, Exceptional, (9 reviews)
"Easy hand's off check in and great communication with the host. The cottage itself was lovely - my friends and I were in town for a wedding and it was the perfect accommodations! Would definitely stay here again! "
United States
Frances D.
The price is ￥39,368
￥46,751 total
includes taxes & fees
Jul 1 - Jul 2
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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 ￥52,566
￥63,257 total
includes taxes & fees
Jul 1 - Jul 2
Enjoy your stay in an antique home in an antique toy museum!
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 ￥28,298
￥75,533 total
includes taxes & fees
Jul 15 - Jul 16
Stunning Glass House nestled in the Vermont wilderness!
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is ￥44,479
￥55,201 total
includes taxes & fees
Jul 8 - Jul 9
Vikings Villages Resort - Double Bed Room
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 ￥26,687
￥50,540 total
includes taxes & fees
Jul 17 - Jul 18
The Studio with a View. Bring your dog, too!
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is ￥19,409
￥34,506 total
includes taxes & fees
Jul 1 - Jul 2
Private bed with En-suite bathroom Marigold 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

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent
"Great hotel with a beautiful view of the river. Staff are warm and helpful. The location is relatively close to Brattleboro and Putney where there is shopping and restaurants. The rooms are spacious, updated and very clean. Room 206 is perfect for sitting on the balcony overlooking the river. For boaters, canoers, kayakers, etc there is a dock on the property where you can put in. Biggest drawback is that there is no food on the property but they do have complimentary bottles of water, hot water for tea and coffee."
Jane 1-night trip
Posted 3 hours ago
Riverside Hotel, an Ascend Collection 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?

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?

Loring Field and Birch Point are a couple of lovely local spots to get outside and enjoy nature. While here, Winchester Speedpark 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.