Cheshire County Holiday Rentals: Short-Term Accommodations for Rent

Holiday Rentals in Cheshire County
United States of America
Holiday Rentals
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Our top choices for Cheshire County holiday rentals

A rustic cabin with a covered porch, a small shed, and outdoor seating.

A circular skylight with a view of trees through the glass.

A tent with a black grill, a table with a laptop, and a chair.

A wood-burning stove with a fire inside, set against a lattice wall.

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

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

Hinsdale

10.0 out of 10, Exceptional, (17 reviews)

10/10

Exceptional

(17 reviews)

"Very enjoyable getaway weekend!!"

Adrienne

The price is HK$706

HK$706

HK$1,233 total

includes taxes & fees

31 Aug - 1 Sept

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

A modern kitchen with a wooden countertop, dark cabinets, and a large window.

A home interior with a wooden staircase, a desk with a chair, a refrigerator, and a lamp.

A modern kitchen with a wooden table and benches, a brick column, and a view of the living area.

A hot tub under a covered patio with a wooden deck and a metal railing.

2. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Keene

9.4 out of 10, Exceptional, (25 reviews)

9.4/10

Exceptional

(25 reviews)

"Amazing property and just what we needed for a recharging weekend!"

Jackie D.

The price is HK$1,326

HK$1,326

HK$2,621 total

includes taxes & fees

30 Aug - 31 Aug

Modern Downtown Escape HotTub Fire Pit Games 12ppl

A lakeside park with picnic tables and a concrete walkway.

A forested area with a clear sky and a dirt path.

A beach with a lifeguard tower and a forested hill in the background.

A utility box labeled with the number 1, connected to a wooden structure with metal brackets and PVC pipes.

3. 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$431

HK$638 total

includes taxes & fees

28 Aug - 29 Aug

2 private mountain RV pads for rent. Full hook ups

A house by a lake with a dock and a boat.

A spacious room with large sliding glass doors leading to a backyard with a picnic table and greenery.

A cozy room with a bed, a chair, and a small table. There is a window with a view of greenery outside.

A small, single-story building with a sloped roof, surrounded by snow-covered ground and trees.

4. 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)

10/10

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! "

Rebecca

The price is HK$1,545

HK$1,545

HK$2,382 total

includes taxes & fees

6 Sept - 7 Sept

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

A two-story house with a front porch, a staircase, and a small garden area.

A narrow hallway with a wooden floor, a white door, and a window with blinds.

A dining area with a wooden table, four chairs, and a green placemat.

A neatly made bed with a quilted white duvet and pillows, a bedside table with a lamp, and a door with a golden handle.

5. Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene

Keene

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"Friendly hosts and excellent location to walk to downtown."

Joshua

The price is HK$1,376

HK$1,376

HK$1,705 total

includes taxes & fees

31 Aug - 1 Sept

Central Large 2-bedrooms with office in Keene

A sunlit room with large windows, a bench, and a row of grey sofas.

A paved outdoor area with stone steps leading up to a building.

A kitchen with white cabinets, a built-in oven, and a dishwasher.

A sunlit room with a sectional sofa, a bench, and a ceiling fan.

6. 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

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

Rindge

10.0 out of 10, Exceptional, (25 reviews)

10/10

Exceptional

(25 reviews)

"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "

Dennis F.

The price is HK$1,376

HK$1,376

HK$2,922 total

includes taxes & fees

8 Sept - 9 Sept

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

A modern kitchen with granite countertops, stainless steel appliances, and a central island.

A spacious kitchen with a central island, bar stools, and a fireplace.

A two-story blue house with a front porch, a chimney, and a number '12' on the door.

A room with two leather chairs facing a large window with a stained glass design.

7. 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, (4 reviews)

10/10

Exceptional

(4 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."

Jeremy S.

The price is HK$1,505

HK$1,505

HK$3,810 total

includes taxes & fees

31 Aug - 1 Sept

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

A modern living room with a wooden door, a sofa, a dining table with chairs, and a mounted TV.

A room with a dark door, a window with a view of greenery, a ceiling light, a wooden wall, a TV mounted on the wall, a small table with a basket, and a radiator.

A compact kitchen with a refrigerator, microwave, and oven.

A small, single-story building with a front door and a small window.

8. Cozy Tiny House on Main Street. Fully Renovated.

Cozy Tiny House on Main Street. Fully Renovated.

Dublin

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Very nice well kept and a great location to Monadnock Hospital."

Melissa M.

The price is HK$1,646

HK$1,646

HK$2,493 total

includes taxes & fees

15 Sept - 16 Sept

Cozy Tiny House on Main Street. Fully Renovated.

A cabin with a dock extending into a calm river, surrounded by snow-covered trees and a clear sky.

A spacious living room with a high ceiling, wooden beams, a fireplace, and a dining area with natural light from large windows.

A rustic kitchen with copper cookware, a stone fireplace, and a dining area with natural light.

A cabin with a central deck, two rocking chairs, and a small table.

9. 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)

9.8/10

Exceptional

(26 reviews)

"Awesome few days away great place and surroundings. Jim is always there for you ."

David S.

The price is HK$1,929

HK$1,929

HK$2,960 total

includes taxes & fees

20 Sept - 21 Sept

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

A cabin with a covered porch, large windows, and snow-covered ground.

A grassy area with a fire pit, boats, and trees near a body of water.

A room with a large sliding glass door leading to a snowy outdoor area, a wooden chair, and a small table.

A bridge over a pond surrounded by dense vegetation and trees.

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

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Rindge

8.0 out of 10, Very good, (5 reviews)

8.0/10

Very good

(5 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 ."

David S.

The price is HK$1,560

HK$1,560

HK$2,509 total

includes taxes & fees

27 Sept - 28 Sept

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

A spacious living room with a checkered sofa, a grey sofa, and a patterned rug. There is a staircase leading to another level, and a dining area with a table and chairs.

A bedroom with a four-poster bed, two windows, a nightstand, and a lamp.

A bedroom with a bed, a chair, a nightstand, a lamp, and a window.

A bathroom with a shower, toilet, and sink.

11. 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

9.6 out of 10, Exceptional, (9 reviews)

9.6/10

Exceptional

(9 reviews)

"This was a very cute rental in a beautiful part of New Hampshire, but it was much smaller than we imagined."

Kelly

The price is HK$2,304

HK$2,304

HK$2,857 total

includes taxes & fees

30 Aug - 31 Aug

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

A four-poster bed with a grey bedspread, a wooden nightstand with a lamp, a wooden dresser, and a chair.

A bathroom with a sink, toilet, and shower curtain.

A compact kitchen with white cabinets, a stove, a microwave, and a window above the sink.

A modern living room with a grey sofa, a wooden coffee table, and a TV stand.

12. Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls

Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls

Walpole

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"A cozy little cottage on a beautiful property. Great for 4 adults or a small family "

Sheilah Z.

The price is HK$2,304

HK$2,304

HK$2,857 total

includes taxes & fees

30 Aug - 31 Aug

Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls

Two Adirondack chairs and a fire pit in a grassy field with a forested hill in the background.

A room with two armchairs, a small table with a lamp, and a patterned rug.

A L-shaped sectional sofa with floral cushions, a wooden coffee table, and large windows with a view of greenery.

A spacious hallway with a large window leading to a deck, a staircase, and a patterned rug on the floor.

13. Large Farmhouse with expansive views, firepit 15 min north of Keene

Large Farmhouse with expansive views, firepit 15 min north of Keene

Walpole

The price is HK$3,075

HK$3,075

HK$3,812 total

includes taxes & fees

30 Aug - 31 Aug

Large Farmhouse with expansive views, firepit 15 min north of Keene

A patio area with outdoor furniture, a small garden with purple flowers, and a white building in the background.

A white building with a sign reading "ENTRANCE" and a staircase leading up to it.

A kitchen with wooden cabinets, a bar area, and a shelf with dishes.

A two-story white house with a front porch, stone foundation, and a garden with various plants.

14. Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Walpole

10.0 out of 10, Exceptional, (52 reviews)

10/10

Exceptional

(52 reviews)

"We had a very lovely stay. "

mary c.

The price is HK$2,822

HK$2,822

HK$5,443 total

includes taxes & fees

3 Sept - 4 Sept

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

A kitchen with a brick fireplace, wooden cabinets, a central island with stools, and a large window with plants.

A red house with a flag, surrounded by green grass and trees.

A bedroom with a large bed, a wooden bookshelf, a TV, and a window with a view.

A two-story house with a snow-covered lawn and a lit front door.

15. Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

Dublin

10.0 out of 10, Exceptional, (26 reviews)

10/10

Exceptional

(26 reviews)

"Good place to stay during a wedding week"

Veronique S.

Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

A bathroom with a shower curtain, a shower head, and a small shelf.

A stone pathway with large rocks and a wooden structure in the background.

16. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH

Hinsdale

9.6 out of 10, Exceptional, (7 reviews)

9.6/10

Exceptional

(7 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. "

Allisha C.

The price is HK$529

HK$529

HK$999 total

includes taxes & fees

30 Aug - 31 Aug

Yurt Oasis in the woods of Hinsdale, NH

A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

A kitchen with wooden cabinets, a dining table with chairs, and a view of a balcony.

A spacious living area with a kitchen, two sofas, and a TV.

A lakeside view with a dock, picnic table, and an American flag.

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

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

Stoddard

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Everything was perfect for our weekend stay. Host responded immediately to our questions. House had all the amenities for an enjoyable time!"

Mary P.

The price is HK$2,940

HK$2,940

HK$5,350 total

includes taxes & fees

31 Aug - 1 Sept

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

A wooden cabin with a gabled roof, multiple windows, and a front porch.

A room with a bed, wooden ceiling, and a sliding glass door leading to a snowy outdoor area.

A rustic lodge with a porch, outdoor seating, and a picnic table.

18. 2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac

Rindge

The price is HK$4,226

HK$4,226

HK$6,201 total

includes taxes & fees

8 Sept - 9 Sept

2 Cabins & Sauna on Lake Monomonac

A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

A bedroom with a bed, a dresser, a chair, a television, and a mirror.

A kitchen with wooden flooring, a window with blinds, a small trash can, and a stove.

A library building with a brick facade, large windows, and a sidewalk in front.

19. 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

10.0 out of 10, Exceptional, (41 reviews)

10/10

Exceptional

(41 reviews)

"Wonderful stay! Amazing location!"

Basmattee B.

The price is HK$706

HK$706

HK$1,361 total

includes taxes & fees

1 Sept - 2 Sept

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

A small, single-story house with a front door open, revealing a kitchen area with a sink and cabinets.

A small, single-story cabin with a dark front door and a mailbox, surrounded by trees and a gravel driveway.

A bedroom with a bed, a TV, a wooden bench, and a door.

A residential area with multiple houses, a gravel driveway, and parked vehicles.

20. Cozy Cabin in a rural setting #12 in Temple NH

Cozy Cabin in a rural setting #12 in Temple NH

Temple

9.2 out of 10, Wonderful, (21 reviews)

9.2/10

Wonderful

(21 reviews)

"Amazing best place in nh"

Dean S.

The price is HK$784

HK$784

HK$1,463 total

includes taxes & fees

7 Sept - 8 Sept

Cozy Cabin in a rural setting #12 in Temple NH

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

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent

"Spacious rooms, big balconies overlooking the river, and the whole hotel was VERY clean."

Jason 1-night trip

Posted 5 hours ago

Riverside Hotel, an Ascend Collection Hotel

Hampton Inn Brattleboro

8/10 Good

"Very clean. Good full breakfast."

Barbara 1-night trip

Posted 1 day ago

Hampton Inn Brattleboro

Gardner Inn

10/10 Excellent

"My room was clean and comfortable. The staff was excellent and very responsive to any and all requests and to even just chat with. Plenty of parking with a special spot for a Veteran - Because We Served - to park."

Sharon 3-night trip

Posted 1 day ago

Gardner Inn