Cheshire County Vacation Rentals from CA $308: Short-Term Rentals for 2026

Top Cities in Cheshire County

A forest path with autumn foliage, rocks, and ferns.

Our top choices for Cheshire County vacation rentals

A wooden deck with a rustic outdoor seating area, including Adirondack chairs and a small table, surrounded by a forested area with a wooden structure in the background.

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

Hinsdale

Adrienne

CA $212 total

includes taxes & fees

Nov 17 - Nov 18

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

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

Rindge

clifford t.

CA $360 total

includes taxes & fees

Nov 16 - Nov 17

A wooden deck with a grill and propane tank, surrounded by trees.

3. Yurt Oasis in the woods of Hinsdale, NH

Hinsdale

Ian C.

CA $209 total

includes taxes & fees

Nov 18 - Nov 19

A deck with a round table and chairs, surrounded by a white railing, overlooking a lake.

4. "Pondlife" - Waterfront home in a peaceful, wooded setting.

Fitzwilliam

Margaret

CA $402 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Rindge

David S.

CA $401 total

includes taxes & fees

Nov 22 - Nov 23

A modern kitchen with a wooden island, a dining area with a sofa, and a living room with a TV and artwork.

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

Dublin

David W.

CA $427 total

includes taxes & fees

Nov 16 - Nov 17

A covered outdoor deck with a grill, seating area, and a blue shed in the background.

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

Keene

Jeremy S.

CA $653 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Rindge

David S.

CA $448 total

includes taxes & fees

Nov 16 - Nov 17

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

9. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Keene

cody s.

CA $511 total

includes taxes & fees

Nov 19 - Nov 20

A wooden deck with two chairs and a table, overlooking a lake with trees in the background.

10. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

Rindge

Susan G.

CA $534 total

includes taxes & fees

Nov 16 - Nov 17

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

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

Stoddard

Mary P.

CA $862 total

includes taxes & fees

Nov 16 - Nov 17

Three wooden Adirondack chairs on a grassy lawn with a wooden deck and a wooden fence in the background.

12. Cobb Meadow House: Cozy 5 Bedroom Retreat

Dublin

Veronique S.

CA $988 total

includes taxes & fees

Nov 16 - Nov 17

A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

13. Cozy Vermont Tiny Home Get Away

Brattleboro

Anthony L.

CA $135 total

includes taxes & fees

Nov 30 - Dec 1

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

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

Peterborough

Basmattee B.

CA $217 total

includes taxes & fees

Nov 17 - Nov 18

A blue house with a porch, a wooden bench, and a door.

15. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Greenfield

JAMES S.

CA $325 total

includes taxes & fees

Nov 18 - Nov 19

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

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

Temple

Rick C.

CA $308 total

includes taxes & fees

Nov 16 - Nov 17

A bedroom with a bed, a bedside table, and a nightstand. There is a window with blinds and a door leading to the outside.

17. Cozy Cabin in a rural setting #10 In Temple, NH

Temple

Ann S.

CA $288 total

includes taxes & fees

Nov 16 - Nov 17

A wooden staircase leading up to a wooden bridge in a forested area.

18. Wellness Getaway with a Personal Sauna, and Private River Beach!

Newfane

Joseph P.

CA $409 total

includes taxes & fees

Nov 23 - Nov 24

A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

19. 2 Twin beds on 1st floor with En-suite bathroom.

Shelburne Falls

CA $245 total

includes taxes & fees

Nov 16 - Nov 17

A wooden interior with a kitchen, bar area, and dining space.

20. The Studio with a View. Bring your dog, too!

Brattleboro

James M.

CA $326 total

includes taxes & fees

Nov 18 - Nov 19

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Top Cheshire County Hotel Reviews

Pointe at Castle Hill Resort

10/10 Excellent

"We booked a deluxe suite, and it was fantastic — basically a full one-bedroom apartment with a kitchen equipped with all the essentials, including a washing machine and dryer. The location is quiet and peaceful, and the property itself is clean, cozy, and well-maintained. The hotel also has great amenities like a pool, gym, and hot tub — unfortunately, we didn't get a chance to use them this time, but it's a wonderful bonus to have! There were only two small issues: it was a bit tricky to find our room at first since it was located in the far wing of the building, and the heater was rather hard to adjust. Aside from that, our stay was wonderful. We love staying at this hotel and will definitely be back again!"

The Colonial Hotel

8/10 Good

"Overall the place is good but my wife has bad allergies so I usually check the filters in the air system in room, if possible. Well, I did and whoaa. The filters were horrible and certainly not cleaned in months. I took them out and rinsed them in shower. I showed the front desk woman who asked what room. She said she would tell the housekeeping staff. I do not believe they should be the one to have to clean it but, thats my opinion. I never heard anything else from hotel."

Hideaway Inn Mt.Sunapee

10/10 Excellent

"As someone who travels up to New Hampshire frequently, finding a reliable and welcoming place to stay is essential, and the Hideaway Inn at Mt Sunapee absolutely delivered. I stayed here with my two sons, and we had an incredible time. Our room was comfortable and flawlessly clean, and the whole facility feels like a super retro cabin. The property strikes the perfect balance, as it is incredibly family-oriented with endless entertainment for kids, yet maintains a relaxed, well-kept atmosphere that is genuinely great for adults trying to unwind. There was never a dull moment during our stay. The boys spent hours swimming and smiling in the indoor pool, challenging each other to ping pong and chess, and trying to beat the high score on the classic Pac-Man arcade game. The dedicated play area, complete with a pretend ice cream stand and the adorable Hideaway Inns teepee, was a massive hit. It is a fantastic, joyful retreat with something for everyone. We will definitely be back on our next trip north!"

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent

"We loved the size of the room and bathroom. Well-maintained property, very friendly staff. They have an under-utilized dining room on the ground floor with nice views of the river but no offered breakfast, just coffee. Some type of offered breakfast would make this a five star review."

Find out more about Cheshire County

Everything you need to know about Cheshire County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cheshire County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cheshire County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheshire County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheshire County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cheshire County vacation rentals we have selected for you start as low as CA $308 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cheshire County rentals

At Expedia, we put the best Cheshire County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cheshire County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cheshire County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cheshire County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Top Cities in Cheshire County

Jaffrey

Our top choices for Cheshire County vacation rentals

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

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

3. Yurt Oasis in the woods of Hinsdale, NH

4. "Pondlife" - Waterfront home in a peaceful, wooded setting.

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

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

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

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

9. Modern Downtown Escape HotTub Fire Pit Games 12ppl

10. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

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

12. Cobb Meadow House: Cozy 5 Bedroom Retreat

13. Cozy Vermont Tiny Home Get Away

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

15. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

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

17. Cozy Cabin in a rural setting #10 In Temple, NH

18. Wellness Getaway with a Personal Sauna, and Private River Beach!

19. 2 Twin beds on 1st floor with En-suite bathroom.

20. The Studio with a View. Bring your dog, too!

Find vacation rentals that suit your style

Top Cheshire County Hotel Reviews

Pointe at Castle Hill Resort

The Colonial Hotel

Comfort Inn & Suites Brattleboro I-91

Hideaway Inn Mt.Sunapee

Riverside Hotel, an Ascend Collection Hotel

Claremont Motor Lodge

Find out more about Cheshire County