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Cottages in Cheshire County

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Top Cities in Cheshire County

A street with historic buildings, a church steeple, and autumn foliage.
CottagesCottages

Keene

Keene
A pathway surrounded by trees with autumn foliage.
CottagesCottages

Rindge

Rindge

Our top choices for Cheshire County cottages

Exterior

1. Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Westminster
9.6 out of 10, Exceptional, (40 reviews)
"Beautiful location and perfect for a fishing getaway! House was clean and cozy!"
United States
Julianne R.
The price is HK$1,569
HK$3,933 total
includes taxes & fees
7 Sept - 8 Sept
Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board
Property grounds

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

Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Rindge
10.0 out of 10, Exceptional, (37 reviews)
"Place was spotless- loved the QUIET- overall wonderful time!"
United States
Brenda D.
Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Property grounds

3. Cozy cottage on Pleasant Pond

Cozy cottage on Pleasant Pond
Warner
9.4 out of 10, Exceptional, (28 reviews)
"Had a great stay, home is very cozy and the pond out back is beautiful. Great place to take a little break"
United States
Sam F.
Cozy cottage on Pleasant Pond
Exterior

4. Sweet vintage cottage on Mountain View Lake, 2024 updates, next to Lake Sunapee

Sweet vintage cottage on Mountain View Lake, 2024 updates, next to Lake Sunapee
Sunapee
9.0 out of 10, Wonderful, (10 reviews)
"The acorn in a cute little cottage on beautiful Mountain View lake. The cottage had everything we needed for our stay. The host was responsive, friendly and gave great recommendations for area hikes and activities. "
United States
Deb D.
Sweet vintage cottage on Mountain View Lake, 2024 updates, next to Lake Sunapee
Property grounds

5. Cottage beside a waterfall

Cottage beside a waterfall
Wilton
9.8 out of 10, Exceptional, (18 reviews)
"BEAUTIFUL surroundings and very peaceful. Would definitely recommend staying here!! "
United States
Vicki L.
The price is HK$1,255
HK$2,222 total
includes taxes & fees
24 Aug - 25 Aug
Cottage beside a waterfall
Exterior

6. Waterfront Cottage on Scenic Sportsman Pond

Waterfront Cottage on Scenic Sportsman Pond
Fitzwilliam
9.6 out of 10, Exceptional, (48 reviews)
"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

7. Lakeside home. Fishing, paddle boarding, swimming, and easy lake fun.

Lakeside home. Fishing, paddle boarding, swimming, and easy lake fun.
Warner
10.0 out of 10, Exceptional, (61 reviews)
"Had a great time and was very relaxing !"
United States
Jackie C.
Lakeside home. Fishing, paddle boarding, swimming, and easy lake fun.
Exterior

8. The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Chester
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful location, nice yard, and very quiet. The home has real potential but needs some TLC to realize it."
United States
Anonymous traveller
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Property grounds

9. Idyllic Lakefront Cottage Near Mount Sunapee

Idyllic Lakefront Cottage Near Mount Sunapee
Bradford
9.8 out of 10, Exceptional, (7 reviews)
"Very welcoming and well stocked!"
United States
Becky L.
Idyllic Lakefront Cottage Near Mount Sunapee
Interior

10. West Dover Home - 3 Miles to Mount Snow Resort!

West Dover Home - 3 Miles to Mount Snow Resort!
3.0 star property
West Dover
10.0 out of 10, Exceptional, (1 review)
"Beautiful home, spacious, huge back yard. Close to everything you need. Hoping to return soon!!"
United States
Jacqueline
West Dover Home - 3 Miles to Mount Snow Resort!
Exterior

11. Cavalier Cottage B&B

Cavalier Cottage B&B
3.0 star property
Shelburne Falls
9.0 out of 10, Wonderful, (2 reviews)
"Perfect for a quiet, weekend getaway. We went to celebrate our 5 year anniversary and brought our dog, Ollie. Ollie's a very timid and nervous guy, but he felt very comfortable here. We went during the winter, but would be interested in returning in the summer because there seems to be a lot of outdoor activities (white water rafting, fishing, hiking). "
United States
jennifer
Cavalier Cottage B&B
Exterior

12. Vermont Country Cottage (Near Village)

Vermont Country Cottage (Near Village)
Londonderry
9.4 out of 10, Exceptional, (14 reviews)
"Convenient location for the event and places we wanted to visit!"
United States
Joe A.
Vermont Country Cottage (Near Village)
Exterior

13. 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
Wilmington
8.6 out of 10, Excellent, (76 reviews)
"Absolutely charming cottage in a beautiful and convenient location. Nicely equipped with a dishwasher and washer and dryer. Elegant and updated bathrooms. The home was clean and very comfortable. The only negative was that the mattresses could be replaced."
United States
Bronwyn
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Property grounds

14. Cozy Crescent Cottage-ON THE WATER-Near Mt Sunapee-Great Fishing-Pet friendly

Cozy Crescent Cottage-ON THE WATER-Near Mt Sunapee-Great Fishing-Pet friendly
Lempster
10.0 out of 10, Exceptional, (39 reviews)
"Talk about an ideal location! Staying here was a real treat. All the comforts of home and so much natural beauty. "
United States
nicole l.
Cozy Crescent Cottage-ON THE WATER-Near Mt Sunapee-Great Fishing-Pet friendly
Exterior

15. Walk to Sunapee - Screened Porch Bliss + Cool AC

Walk to Sunapee - Screened Porch Bliss + Cool AC
Blodgett Landing
10.0 out of 10, Exceptional, (11 reviews)
"The house was immaculate, cozy, and had everything we needed. The host was very helpful. Would book again!"
United States
Tyler W.
Walk to Sunapee - Screened Porch Bliss + Cool AC
Exterior

16. Cottage Lake Nubanusit

Cottage Lake Nubanusit
Nelson
10.0 out of 10, Exceptional, (3 reviews)
"Me and the wife wanted a place to get away from the daily grind. This small cabin was perfect."
United States
Stephen P.
Cottage Lake Nubanusit
Exterior

17. Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
10.0 out of 10, Exceptional, (13 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 HK$1,632
HK$2,503 total
includes taxes & fees
7 Sept - 8 Sept
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

18. Charming Sunapee Tiny Home: Walk to Lake + Cool AC

Charming Sunapee Tiny Home: Walk to Lake + Cool AC
Blodgett Landing
10.0 out of 10, Exceptional, (5 reviews)
"This cabin was perfect for a ski getaway with our pup! Sarah was kind and communicative - she helped us troubleshoot a water issue that was a result of the cold temperatures. The kitchen was incredibly well equipped, check in/out easy, and the cabin was super comfortable. Roads were cleared enough for our 2 wheel drive sedan to pass easily. We hope to come back! "
United States
Amelia D.
Charming Sunapee Tiny Home: Walk to Lake + Cool AC
Exterior

19. Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!

Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!
Newbury
10.0 out of 10, Exceptional, (38 reviews)
"This is the best VRBO rental ever. Host paid attention to every detail, our family was really impressed. "
United States
Jason T.
Cozy cabin nestled in the woods, 5 minutes to Sunapee Mountain & lake!
Property grounds

20. Family & Dog-Friendly Lakeside Retreat 15-min to Mount Sunapee

Family & Dog-Friendly Lakeside Retreat 15-min to Mount Sunapee
Sunapee
10.0 out of 10, Exceptional, (44 reviews)
"Excellent property and host. Highly recommended. We plan to be back in the future."
United States
Luciano P.
Family & Dog-Friendly Lakeside Retreat 15-min to Mount Sunapee
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"The breakfast was great. The staff was very friendly."
Greg 2-night trip
Posted 9 hours ago
Hampton Inn Brattleboro

Find out more about Cheshire County

Cheshire County Cottages information

Number of reviews
465
Accommodation
182 Cottages
Lowest Price
HK$2,222
Highest Price
HK$3,933

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