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Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Top Cities in Cheshire County

Keene featuring a city and a church or cathedral
CottagesCottages

Keene

Keene

Cottages in Cheshire County

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

Cottage in Wilmington

8.6 out of 10, Excellent, (64)
"Great location and super cute"
United States
Jeff S.
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Property grounds
Cottage beside a waterfall

Cottage in Wilton

9.8 out of 10, Exceptional, (10)
"What a unique place to stay with a waterfall in the backyard! Quiet, beautiful grounds on the property. Clean, private and well appointed. "
United States
Marcella J.
$265 nightly
The price is $288
Dec 8 - Dec 9
Total with taxes and fees
Cottage beside a waterfall
Terrace/patio
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Cottage in Rindge

10.0 out of 10, Exceptional, (22)
"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.
$340 nightly
The price is $368
Dec 8 - Dec 9
Total with taxes and fees
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock
Exterior
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

Cottage in Chester

10.0 out of 10, Exceptional, (18)
"The house is absolutely beautiful - Check in super easy"
United States
Dawn J.
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior
Vermont Country Cottage (Near Village)

Cottage in Londonderry

9.4 out of 10, Exceptional, (14)
"Convenient location for the event and places we wanted to visit!"
United States
Joe A.
Vermont Country Cottage (Near Village)
Exterior
Rare new Home on Lake Whitingham. Semi-priv beach

Cottage in Wilmington

10.0 out of 10, Exceptional, (6)
"Very nice place."
United States
michael r.
Rare new Home on Lake Whitingham. Semi-priv beach
Cottage (3 Bedrooms) | Interior
Lakefront Bradford Cottage w/ Dock, Near Skiing!

Cottage in Bradford

3.0 star property
Lakefront Bradford Cottage w/ Dock, Near Skiing!
Exterior
Waterfront Cottage on Scenic Sportsman Pond

Cottage in Fitzwilliam

9.6 out of 10, Exceptional, (44)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
United States
Cathy M.
Waterfront Cottage on Scenic Sportsman Pond
Exterior
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Cottage in Westminster

9.6 out of 10, Exceptional, (29)
"Nice location and a very cool place to stay "
United States
Samson M.
$341 nightly
The price is $374
Dec 9 - Dec 10
Total with taxes and fees
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Exterior
2 queen and 2 twin beds

Cottage in Milford

9.6 out of 10, Exceptional, (14)
"Great location. Very quite and had everything we needed."
United States
Eddie M.
2 queen and 2 twin beds
Exterior
Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min

Cottage in Rindge

10.0 out of 10, Exceptional, (16)
"Loved the water front, using the kayaks was great. The back deck was amazing for get togethers. The house was clean and comfortable. Definitely planning to return."
United States
Valerie R.
Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min
Exterior
Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Cottage in Rindge

10.0 out of 10, Exceptional, (36)
"Cottage is rustic and very comfortable, with everything you need for an enjoyable stay. The waterfront is beautiful and so peaceful, and the view of Monadnock is incredible. Warm water to swim or float, great fishing from the dock, and the owners are super nice. We made some great memories, and would definitely return!"
United States
Jennifer P.
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
House (4 Bedrooms) | Interior
Historic Home w/ Modern Updates on < 4 Acres

Cottage in Royalston

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great place. Enjoyed our stay. Wish it wasn’t raining so we could’ve enjoyed more of the outdoors."
United States
Melissa
Historic Home w/ Modern Updates on < 4 Acres
House (3 Bedrooms) | Interior
Near Hiking & Skiing: Home in Wilmington!

Cottage in Wilmington

3.0 star property
10.0 out of 10, Exceptional, (1)
"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."
United States
Donna
Near Hiking & Skiing: Home in Wilmington!
Exterior
Brook Road Cabin

Cottage in Goshen

3.5 star property
7.8 out of 10, Good, (9)
"In the aftermath of 30+” of snow we dug out and sought a new location with power and hot showers. How blessed we were to find this gem. A point of refuge and some much needed R&R. Cabin was quaint, warm, and comfortable, and the host was attentive and welcoming. Thank you for this port in the storm. 😊"
United States
Jill
$270 nightly
The price is $293
Dec 8 - Dec 9
Total with taxes and fees
Brook Road Cabin
Interior
Cottage on Partridge Pond

Cottage in Westminster

10.0 out of 10, Exceptional, (25)
"Such a cute place..loved the house, the lake and the amenties and special touches...we.will be back!"
United States
Ann N.
Cottage on Partridge Pond
House (4 Bedrooms) | Interior
Near Skiing & Hiking: Quiet Home in West Wardsboro

Cottage in West Wardsboro

3.0 star property
Near Skiing & Hiking: Quiet Home in West Wardsboro
House (5 Bedrooms) | Interior
Pet-friendly Claremont Vacation Rental!

Cottage in Claremont

3.0 star property
Pet-friendly Claremont Vacation Rental!
Exterior
Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!

Cottage in Newbury

10.0 out of 10, Exceptional, (30)
"This was a last-minute booking and we could not have been more happy with itHow’s this beautifully decorated, beds are comfortable and hosts were very easy to work with!"
United States
Elizabeth R.
Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!
Property grounds
Cozy cottage on Pleasant Pond

Cottage in Warner

9.4 out of 10, Exceptional, (25)
"This was our second time at the property and it was even better this time! It’s so nice and peaceful. This is our kids and fur babies favorite place to go, the only bad part was having to leave!!Thanks again it was amazing!"
United States
Shane P.
Cozy cottage on Pleasant Pond
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 Cheshire County Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Great place to stay while skiing at okemo"
Ken 1-night trip
Posted 14 hours ago
Pointe at Castle Hill Resort

Find out more about Cheshire County

Cheshire County Cottages information

Number of reviews
327
Accommodation
181 Cottages
Lowest Price
$288
Highest Price
$374

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