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Check prices for these dates

In two weeks
12 June - 14 June
In two months
24 July - 26 July
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Winchester cottages

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 AU$407
includes taxes & fees
1 June - 2 June
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"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 ❤️"
United States
sarah
The price is AU$574
includes taxes & fees
15 June - 16 June
Hiking Trails On-site: Cozy Falls Brook Cabin
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 AU$481
includes taxes & fees
8 June - 9 June
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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

Econo Lodge Brattleboro South

Econo Lodge Brattleboro South

6/10 Okay
"VERY PLAIN BUT CLEAN ROOM.... OK FOR AN OVERNIGHT"
Patricia 1-night trip
Posted 1 hour ago
Econo Lodge Brattleboro South

Find out more about Winchester

Winchester Cottages information

Number of reviews
20
Accommodation
55 Cottages
Lowest Price
AU$407
Highest Price
AU$574

Frequently asked questions

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.