Cheshire County Holiday Rentals

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Our top choices for Cheshire County holiday rentals

Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (22 reviews)
"Great time easy to get to clean quiet and peaceful definitely would recommend for romantic getaway "
United States
Garrett B.
The price is HK$2,154
HK$2,661 total
includes taxes & fees
3 Jun - 4 Jun
Owl's Nest Treehouse
Terrace/patio

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
9.8 out of 10, Exceptional, (14 reviews)
"Stacy and her husband were very communicative and accommodating. We had everything we needed in the yurt and they provided us with some extra supplies as well. Would definitely stay again!"
United States
Gina M.
The price is HK$705
HK$1,233 total
includes taxes & fees
31 May - 1 Jun
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
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 HK$1,458
HK$2,177 total
includes taxes & fees
3 Jun - 4 Jun
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
9.8 out of 10, Exceptional, (26 reviews)
"Host was incredibly friendly and accommodating and the cabin was nothing short of beautiful"
United States
Moose C.
The price is HK$1,858
HK$2,832 total
includes taxes & fees
3 Jun - 4 Jun
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Exterior

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock
Rindge
7.6 out of 10, Good, (4 reviews)
"Hit the jackpot at this stay .Awesome area with many things to keep busy outside ,hiking all around ,lake for all kind of activities .Jim was a great host filled us in on activities in the area and was a message away for any help u may need .I will be back ."
United States
David S.
The price is HK$1,498
HK$2,399 total
includes taxes & fees
3 Jun - 4 Jun
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
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 HK$2,243
HK$2,749 total
includes taxes & fees
9 Jun - 10 Jun
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Outdoor dining

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is HK$431
HK$638 total
includes taxes & fees
29 May - 30 May
2 private mountain RV pads for rent. Full hook ups
Property grounds

John's Mountain Hideaway

John's Mountain Hideaway
Jaffrey
The price is HK$1,967
HK$3,843 total
includes taxes & fees
4 Jun - 5 Jun
John's Mountain Hideaway
Fridge, microwave, oven, stovetop

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (3 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is HK$1,591
HK$3,826 total
includes taxes & fees
8 Jun - 9 Jun
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Exterior

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston

Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Stoddard
10.0 out of 10, Exceptional, (2 reviews)
"Everything was perfect for our weekend stay. Host responded immediately to our questions. House had all the amenities for an enjoyable time!"
United States
Mary P.
The price is HK$2,742
HK$5,032 total
includes taxes & fees
31 May - 1 Jun
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Property grounds

Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
10.0 out of 10, Exceptional, (2 reviews)
"Cozy and clean yurt in the woods surrounded by sounds of hooting owls and a super friendly and help host made for the perfect family weekend. Can’t wait to plan another stay. Made roughing it not rough at all. "
United States
Allisha C.
The price is HK$649
HK$1,129 total
includes taxes & fees
1 Jun - 2 Jun
Yurt Oasis in the woods of Hinsdale, NH
Exterior

2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is HK$3,990
HK$5,834 total
includes taxes & fees
1 Jun - 2 Jun
2 Cabins & Sauna on Lake Monomonac
Smart TV

Cozy Cabin in a Rural Setting #16 near Temple,NH

Cozy Cabin in a Rural Setting #16 near Temple,NH
Temple
9.4 out of 10, Exceptional, (20 reviews)
"Amazing place very happy will stay again 10 stars "
United States
Dean S.
The price is HK$1,081
HK$1,802 total
includes taxes & fees
15 Jun - 16 Jun
Cozy Cabin in a Rural Setting #16 near Temple,NH
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"Very clean, cozy and lots of nice plants! "
United States
Mary
The price is HK$910
HK$1,576 total
includes taxes & fees
8 Jun - 9 Jun
Lovely 2nd Floor Apartment
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 HK$1,199
HK$3,213 total
includes taxes & fees
27 Jun - 28 Jun
Hiking Trails On-site: Cozy Falls Brook Cabin
Property grounds

Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (13 reviews)
"BEAUTIFUL surroundings and very peaceful. Would definitely recommend staying here!! "
United States
Vicki L.
The price is HK$1,254
HK$2,253 total
includes taxes & fees
31 May - 1 Jun
Cottage beside a waterfall
Exterior detail

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Peterborough
9.8 out of 10, Exceptional, (35 reviews)
"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"
United States
Mark
The price is HK$670
HK$1,322 total
includes taxes & fees
3 Jun - 4 Jun
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is HK$533
HK$2,550 total
includes taxes & fees
31 May - 1 Jun
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Interior

Cozy Cabin in a Rural setting-14

Cozy Cabin in a Rural setting-14
Temple
9.4 out of 10, Exceptional, (8 reviews)
"Place was a very nice stay, area was close to nice places."
United States
Rui V.
The price is HK$991
HK$1,561 total
includes taxes & fees
2 Jun - 3 Jun
Cozy Cabin in a Rural setting-14
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

Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2/10 Terrible
"The building needs a total rehab"
Susan 1-night trip
Posted 2 hours ago
Days Inn by Wyndham Keene NH