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Compare 40 Cottages in Winchester with updated reviews, rates, and availability.

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cottage on Partridge Pond
Lake

Cottage on Partridge Pond

10.0 out of 10, Exceptional, (17)
"Lovely home with a small dock in a large pond! Kayaks in the back yard. Beautiful looking out to the pond. Very comfortable home. Hosts are very responsive. We would definitely stay here again. Nice job!"
Cottage on Partridge Pond
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Exterior

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

10.0 out of 10, Exceptional, (14)
"The property is lovely. It suited our needs and fully equipped. "
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
Exterior

VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula

10.0 out of 10, Exceptional, (4)
"This property was great. Wonderfully modern lake front home. Recommend renting the pontoon to fish for larger fish. Kayaks, Paddleboards, great restaurants and sauna. Picture perfect scenery. "
VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula
Waterfront Cottage on Scenic Sportsman Pond
154 Acre sportsman's Pond, for fishing & boating. Flat boards to swim off.

Waterfront Cottage on Scenic Sportsman Pond

9.6 out of 10, Exceptional, (41)
"Sportsman's Pond and Blueberry Cottage provided the ideal location for disconnecting from the noise and busyness of every day life. The pond was beautifully serene, without outboard motors, jet skis, etc. The fall colors were gorgeous. The hosts provided every sort of watercraft one might want. I kayaked everyday exploring the shoreline and watching for birds. The cottage was well equipped, the bed was comfortable and an assortment of chairs and couches were available for lounging, viewing the...
Waterfront Cottage on Scenic Sportsman Pond
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
Beach

Cottage on Laurel Lake, Private lake access, picture perfect sunsets

9.4 out of 10, Exceptional, (3)
"We loved the lake and the location. Very nice lake. My kids loved swimming, kayaks and paddle boats. Lovely dock with gorgeous sunset. House is very rustic. The stairs are steep and slippery. Could use a handle rail for safety and may not be appropriate for those with small kids or mobility issues. Beds very small. Screened porch room had some defects in the screen and because of this there were lots of bugs. Otherwise comfortable and very fun. Owners responsive and cabin quite cute and...
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Mt. Monadnock from the shore

Vacationer's oasis on the waterfront of picturesque Pearly Pond.

10.0 out of 10, Exceptional, (28)
"This pearl of an oasis is on Pearly Pond with a breath-taking view of Mount Watchusett. Nestled in a quiet cove, it is still close to local amenities, trails and restaurants. The cabin has everything a person could image to bring on vacation such as nice cookware, beach towels, and games. The home boasts a lovely screened in porch and a beautiful dock with canoe and kayak. We highly recommend this cabin. Gary and Linda are consumate hosts!!"
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Charming Jaffrey Cottage w/ Deck & Grill!
Jaffrey Vacation Rental | 4BR | 1.5BA | 1,800 Sq Ft | Steps Required

Charming Jaffrey Cottage w/ Deck & Grill!

10.0 out of 10, Exceptional, (39)
"Stayed four nights. Perfect weather and the foliage was fabulous.The cottage was ideal for us. Tastefully decorated and everything labeled. Wish we lived closer so we could go again in other seasons."
Charming Jaffrey Cottage w/ Deck & Grill!
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Miscellaneous

Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe

9.6 out of 10, Exceptional, (4)
"This lake house has it all. Views, nature, wildlife and so many things to do. Kayak, paddleboard, fishing, boating and so much more! Highly recommend! The host is top notch! "
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions
d4dfddeb-ca93-4c46-84bb-9f6f05aa287b

Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions

10.0 out of 10, Exceptional, (6)
"Short time we had there but everything was great would love to stay again for personal trip and see more of the farm "
The price is SAR 917
SAR 1,104 total
includes taxes & fees
2 Jan - 3 Jan
Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions
Historic Home w/ Modern Updates on < 4 Acres
Exterior

Historic Home w/ Modern Updates on < 4 Acres

3.0 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on < 4 Acres
Cozy Tiny House on Main Street. Fully Renovated.
Most of the Tiny House. Looking out from the bedroom doorway

Cozy Tiny House on Main Street. Fully Renovated.

10.0 out of 10, Exceptional, (4)
"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!
Living area

Cozy Falls Brook Cabin: Hike & Swim On-site!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
Cozy Falls Brook Cabin: Hike & Swim On-site!
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Exterior

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

3.0 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!
Jacksonville Cabin w/ Wraparound Deck & Views
Terrace/patio

Jacksonville Cabin w/ Wraparound Deck & Views

3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

3.0 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!
Charming Jaffrey Cottage w/ Deck & Grill!
Property grounds

Charming Jaffrey Cottage w/ Deck & Grill!

3.0 star property
Charming Jaffrey Cottage w/ Deck & Grill!
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Exterior

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Cottage Lake Nubanusit
Exterior

Cottage Lake Nubanusit

10.0 out of 10, Exceptional, (2)
"A lovely patina from years of caring use, authentic, genuine, simple and very comfortable. Well equipped, everything works. Screen porch is perfect. Dock and shoreline easy and very pretty, perfect for kayaks/canoes. We look forward to a future stay!"
Cottage Lake Nubanusit
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Private kitchen

Peaceful Marlboro Vacation Rental w/ Sauna & Yard!

3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
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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Other property types in Winchester

Charming Waterfront Log Cabin
Exterior

Charming Waterfront Log Cabin

9.6 out of 10, Exceptional, (37)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Hilltop Home with Great Views
Exterior

Hilltop Home with Great Views

9.2 out of 10, Wonderful, (12)
"Michelle made our experience super easy and memorable! Drive up a private road and a pretty steep hill (4wd a must in winter) to a secluded, beautiful house with plenty of space. Just you and nature. The house itself has all the amenities - full kitchen, sitting areas, and even a wood stove that Michelle started up before we got there. Beds are comfortable, and the bathrooms have insane mountaintop views. Michele even left a few eggs for starter breakfast which was much appreciated. You can’t...
Hilltop Home with Great Views
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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