Photo by Donny Campos

Search Winchester Cottages

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

Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, 34 reviews
"We live in three different states and are usually only all together once a year at the oldest sister’s house. This year we decided to go away together after attending a graduation party. Lots of time to talk and laugh! This house was perfect for that!"
Cozy Cottage Along Idyllic Green River
Cottage Lake Nubanusit
10.0 out of 10, Exceptional, 1 review
"Me and the wife wanted a place to get away from the daily grind. This small cabin was perfect."
Cottage Lake Nubanusit
Charming Jaffrey Cottage w/ Deck & Grill!
10.0 out of 10, Exceptional, 34 reviews
"Loved everything about it!"
Charming Jaffrey Cottage w/ Deck & Grill!
Save an average of 15% on thousands of hotels when you're signed in
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, 25 reviews
"I’m forever overjoyed with the way people transform small spaces and this cabin is on point! I never even knew the lake was right behind the place! How my dog and I enjoyed our daily walks along the lake road. The lake is a paddlers paradise. Most days I was the only one out there. It IS cabin living so you’ll have some occasional hard water experiences and the fyi g insects are hatching now so they like to visit. Gratefully my dog loves to eat them. Enjoy.! We loved it and will be back for...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, 35 reviews
"Had a wonderful weekend kayaking and fishing. Very private and quiet. Great relaxing spot in nature"
Waterfront Cottage on Scenic Sportsman Pond
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
9.0 out of 10, Wonderful, 2 reviews
"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
Cottage on Partridge Pond
10.0 out of 10, Exceptional, 11 reviews
"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
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
10.0 out of 10, Exceptional, 24 reviews
"I heard no complaints from our Traveling employees."
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Granite Lake NH Waterfront Cottage with Private Dock and Sandy Swimming Area
Granite Lake NH Waterfront Cottage with Private Dock and Sandy Swimming Area
Historic Home w/ Modern Updates on < 4 Acres
3.5 star property
10.0 out of 10, Exceptional, 1 review
Historic Home w/ Modern Updates on < 4 Acres
Cozy Tiny House on Main Street. Fully Renovated.
10.0 out of 10, Exceptional, 3 reviews
"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.
Cozy Falls Brook Cabin: Hike & Swim On-site!
3.5 star property
Cozy Falls Brook Cabin: Hike & Swim On-site!
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
3.5 star property
10.0 out of 10, Exceptional, 1 review
"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!
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.5 star property
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+"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Jacksonville Cabin w/ Wraparound Deck & Views
3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
3.5 star property
10.0 out of 10, Exceptional, 1 review
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Cozy 'green Mountain Chalet' in Putney Town
3.0 star property
Cozy 'green Mountain Chalet' in Putney Town
The Cortland Cottage-Cozy Post & Beam cottage w/ hot tub in historic Walpole, NH
The price is $250
$457 total
includes taxes & fees
Jun 11 - Jun 12
The Cortland Cottage-Cozy Post & Beam cottage w/ hot tub in historic Walpole, NH
Don't see what you're looking for?
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

1810 Brook Side Mill/House / EV Level 2 Charging on Site
10.0 out of 10, Exceptional, 59 reviews
"We stayed as part of a business trip. Three floors each with a bathroom was the selling point for our team. Everything was clean and as described. We would stay again!"
1810 Brook Side Mill/House / EV Level 2 Charging on Site
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, 8 reviews
"The house was superb for our family visit! We enjoyed it all! Linda was a perfect hostess…,so attentive!"
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, 25 reviews
"I’m forever overjoyed with the way people transform small spaces and this cabin is on point! I never even knew the lake was right behind the place! How my dog and I enjoyed our daily walks along the lake road. The lake is a paddlers paradise. Most days I was the only one out there. It IS cabin living so you’ll have some occasional hard water experiences and the fyi g insects are hatching now so they like to visit. Gratefully my dog loves to eat them. Enjoy.! We loved it and will be back for...
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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
146
Accommodation
31 Cottages
Lowest Price
$250
Highest Price
$250

Frequently asked questions

Why book your cottage in Winchester with Expedia?
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?
A wonderful way to score cheap cottages in Winchester is with Expedia’s handy filter tool. Narrow down your search by star rating, amenities and budget to nab awesome bargains in a few clicks.
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.

Recent reviews of Winchester hotels
Expedia verified reviews