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Compare 31 Cottages in Winchester with updated reviews, rates, and availability.

Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (24)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Exterior
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, (34)
"Linda was wonderful in her review of the property and was very accommodating in all aspects of our stay. The cottage was well equipped and very comfortable including the mattress. We enjoyed the lake and a little fishing. The area is very nice and we did some exploring. It was very quiet and we rarely even saw anyone while we were on the lake. We hope to return in the spring or summer. Many thanks to Linda and Brad"
Waterfront Cottage on Scenic Sportsman Pond
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (33)
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
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Interior
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
9.0 out of 10, Wonderful, (2)
"It is a fun place for kids with a beautiful lake to enjoy. We made many fun memories and enjoyed our stay very much."
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
Interior
Cottage on Partridge Pond
10.0 out of 10, Exceptional, (11)
"I rented to accommodate family flying in from the Netherlands for a wedding. This house provided peace and quiet and relaxation for them. The home is clean and well stocked, comfortable beds and tastefully decorated. Situated on a lovely little pond, it is a nice getaway."
Cottage on Partridge Pond
Pool
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
10.0 out of 10, Exceptional, (24)
"I heard no complaints from our Traveling employees."
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Fridge, microwave, stovetop, dishwasher
Charming Jaffrey Cottage w/ Deck & Grill!
10.0 out of 10, Exceptional, (34)
"Loved everything about it!"
Charming Jaffrey Cottage w/ Deck & Grill!
Exterior
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Private kitchen
Granite Lake NH Waterfront Cottage with Private Dock and Sandy Swimming Area
Granite Lake NH Waterfront Cottage with Private Dock and Sandy Swimming Area
Interior
Historic Home w/ Modern Updates on < 4 Acres
3.5 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres
Exterior
Cozy Tiny House on Main Street. Fully Renovated.
10.0 out of 10, Exceptional, (3)
"I was in Dublin visiting my daughter who goes to high school here and it was the perfect place for me to stay and she stayed with me two nights. The owner thought of everything you would need. It was super clean and everything looked brand new. Really well decorated. The owner was super helpful and I’m sure I’ll be back before my girl graduates. Highly recommend!"
Cozy Tiny House on Main Street. Fully Renovated.
Interior
Cozy Falls Brook Cabin: Hike & Swim On-site!
3.5 star property
Cozy Falls Brook Cabin: Hike & Swim On-site!
Interior
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
3.5 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Interior
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.5 star property
10.0 out of 10, Exceptional, (1)
"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+"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Interior
Jacksonville Cabin w/ Wraparound Deck & Views
3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Interior
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
3.5 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Interior
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Interior
Cozy 'green Mountain Chalet' in Putney Town
3.0 star property
Cozy 'green Mountain Chalet' in Putney Town
TV, books
Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions
10.0 out of 10, Exceptional, (3)
"My family and I thoroughly enjoyed staying at the property. The surrounding area is green and beautiful. The house is very charming and the linens are incredibly comfortable. We all wholeheartedly recommend this stay."
The price is $284
$346 total
includes taxes & fees
May 28 - May 29
Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions
TV, fireplace
Family Cottage On Pristine Lake Nubanusit
Family Cottage On Pristine Lake Nubanusit
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See all available properties in Winchester
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.

Other property types in Winchester

Interior
Charming Waterfront Log Cabin
10.0 out of 10, Exceptional, (24)
"Wonderful place it’s are 3rd time staying there an you can’t beat the location, pond view or the nature surrounding you. An a very fast response. I will be staying agsin!"
The price is $189
$407 total
includes taxes & fees
Jun 11 - Jun 12
Charming Waterfront Log Cabin
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (24)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (33)
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
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.

Winchester Cottages information

Number of reviews
145
Accommodation
31 Cottages
Lowest Price
$284
Highest Price
$284

Frequently asked questions

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Booking a cottage in Winchester is as easy as entering your travel dates and picking an ideal place for a vacation in the outdoors. From chic retreats to budget-friendly stays and cottages that come with amenities like a kitchenette, Expedia has something for all styles. As for the best deals around? We’ve got you covered!
How can I find cheap cottages in Winchester?
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What is there to do in Winchester near my cottage?
Whatever you love to do, Winchester has a whole lot to keep you on the move. Pisgah State Park, Asbury United Methodist Church and Little Monadnock Mountain are on most visitors’ sightseeing itineraries. Don’t head home without exploring Birch Point, Madame Sherri Forest and Thomas Aquinas College either. With Expedia’s hotel deals in Winchester, you’ll be able to discover even more fantastic attractions like these with the money you save.

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