Winchester Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

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 ￥8,617
￥12,750 total
includes taxes & fees
May 12 - May 13
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, (11 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 ￥14,101
￥24,650 total
includes taxes & fees
May 12 - May 13
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
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 ￥34,493
￥53,066 total
includes taxes & fees
May 17 - May 18
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, (35 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 ￥14,885
￥28,051 total
includes taxes & fees
May 27 - May 28
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
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 ￥25,735
￥41,353 total
includes taxes & fees
May 12 - May 13
Cabin & 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 ￥31,179
￥38,100 total
includes taxes & fees
May 12 - May 13
Vikings Villages Resort - Double Bed Room
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (53 reviews)
"Very clean, cozy and lots of nice plants! "
United States
Mary
The price is ￥18,191
￥31,871 total
includes taxes & fees
May 24 - May 25
Lovely 2nd Floor Apartment
Interior

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 ￥24,943
￥41,853 total
includes taxes & fees
May 17 - May 18
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is ￥18,614
￥43,194 total
includes taxes & fees
May 13 - May 14
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
House (4 Bedrooms) | Interior

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
The price is ￥23,972
￥81,713 total
includes taxes & fees
May 12 - May 13
Outdoor Adventure Hub! Family Home in West Dover
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 ￥25,069
￥44,923 total
includes taxes & fees
May 28 - May 29
Wellness Getaway with a Personal Sauna, and Private River Beach!
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 ￥27,497
￥58,224 total
includes taxes & fees
May 12 - May 13
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 price is ￥21,152
￥42,467 total
includes taxes & fees
May 12 - May 13
The Studio with a View. Bring your dog, too!
Exterior

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is ￥25,382
￥47,602 total
includes taxes & fees
May 12 - May 13
Rose wisteria 4 guests 2 bedrooms-full+queen beds
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 ￥13,318
￥31,869 total
includes taxes & fees
May 31 - Jun 1
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
4 bedrooms, travel crib, internet, bed sheets

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
West Dover
10.0 out of 10, Exceptional, (5 reviews)
"The house was just as listed. Everything we needed was there for us upon arrival. The host is amazing and was happy to welcome us in their home. We would definitely come back"
United States
Louis
The price is ￥21,465
￥85,359 total
includes taxes & fees
May 12 - May 13
Outdoor Adventure Hub! Family Home in West Dover
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 ￥11,010
￥59,672 total
includes taxes & fees
May 12 - May 13
Chalet Mount Snow/Stratton Skiing/hiking
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is ￥25,523
￥47,012 total
includes taxes & fees
May 13 - May 14
Family Friendly Hilltop House In Putney Vermont
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 ￥35,073
￥41,795 total
includes taxes & fees
May 12 - May 13
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Smart TV

Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.
Dublin
10.0 out of 10, Exceptional, (5 reviews)
"Very nice well kept and a great location to Monadnock Hospital."
United States
Melissa M.
The price is ￥23,502
￥37,584 total
includes taxes & fees
May 13 - May 14
Cozy Tiny House on Main Street. Fully Renovated.
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

Latchis Hotel

Latchis Hotel

8/10 Good
"Lots to do nearby. This is a converted office building. Appreciated the quirkiness of the property; however, it was fairly poorly maintained - quite dirty in the stairwells and hallways, dank smell in the room, dated furniture and linens. We liked the location and are easy going... so these things did not bother us, but just be aware if you're more discerning..."
Karyn 1-night trip
Posted 2 hours ago
Latchis 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?

Barden State Wildlife Management Area and Rhododendron State Park are a couple of lovely local spots to get outside and enjoy nature. While here, Winchester Speedpark 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.