Cheshire County Vacation Rentals from $94: Search Short-Term Rentals

A covered bridge with a sign reading "Ashuelot Covered Bridge 1864" and a warning about the fine for riding or driving over it.

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Top cities in Cheshire County

A street with a clock, red brick buildings, and autumn leaves.

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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

$137 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

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

Rindge

clifford t.

$230 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

3. Yurt Oasis in the woods of Hinsdale, NH

Hinsdale

Ian C.

$135 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

$260 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Rindge

David S.

$235 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

$272 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

$422 nightly

Nov 16 - Nov 17

Total with taxes and fees

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.

$272 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

$341 nightly

Nov 19 - Nov 20

Total with taxes and fees

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.

$345 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

$557 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

$626 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

13. Cozy Vermont Tiny Home Get Away

Brattleboro

Anthony L.

$84 nightly

Nov 30 - Dec 1

Total with taxes and fees

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.

$144 nightly

Nov 17 - Nov 18

Total with taxes and fees

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.

$204 nightly

Nov 18 - Nov 19

Total with taxes and fees

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.

$200 nightly

Nov 16 - Nov 17

Total with taxes and fees

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.

$187 nightly

Nov 16 - Nov 17

Total with taxes and fees

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.

$253 nightly

Nov 23 - Nov 24

Total with taxes and fees

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

$153 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Brattleboro

James M.

$204 nightly

Nov 18 - Nov 19

Total with taxes and fees

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Find vacation rentals that suit your style

Top Cheshire County Hotel Reviews

A rustic wooden cabin with a thatched roof, a wooden deck, and a stone wall.

Vikings Villages Resort

Guilford

10/10 Excellent

Diego

A two-story house with a large porch and multiple windows, surrounded by autumn foliage.

Shelburne Springs Hotel

Shelburne Falls

10/10 Excellent

Brian

Centennial House

Northfield

10/10 Excellent

My husband and I have never stayed at a B&B. We were looking for a nearby weekend get-away and found The Centennial House on an on-line search. The Hosts Joan & Steve were very hospitable and knowledgable of the area and it's history and attractions. The surrounding area, the room and the breakfast were beautiful, comfortable and delicious!! Our first B&B experience was excellent, thank you Joan & Steve. Until we meet again, Bill & Anne

Anonymous traveler

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

Four Columns Inn

Newfane

10/10 Excellent

Nettie

A dock extending into a calm lake, surrounded by lush greenery.

Riverside Hotel, an Ascend Collection Hotel

West Chesterfield

10/10 Excellent

James

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

A triangular wooden structure with a bench and a table, surrounded by lush greenery and a building in the background.

Otherland Hotel

Newfane

10/10 Excellent

The property is very well maintained and decorated. The room and bathroom are very clean. It has two very nice common area with 2 big windows that made them bright and sunny and cozy. It's also along a major highway so it's easy to find. The owners/operators of this hotel are very kind, thoughtful and accomodating to the needs of their guests. I especially and directly experienced their wonderful hospitality as a disabled person in a wheelchair. When I inquired about the accessibility of...

Rosalie

A wooden sign with an arrow pointing to the right, labeled "CHICKENS".

The Wilmington Inn

Wilmington

10/10 Excellent

Sophia

A large white building with a stone wall and a lawn covered in fallen leaves.

Colonel Williams Inn

Brattleboro

10/10 Excellent

Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...

Ann

A historic building with a prominent corner turret and a wrap-around porch.

Rosewood Country Inn

Bradford

10/10 Excellent

Anonymous traveler

A wooden table set with plates, cutlery, and a folded napkin.

The Carriage Barn Inn

Keene

10/10 Excellent

Richard

A covered porch with Adirondack chairs and a table with wine glasses, overlooking a lake and lush greenery.

The Maguire House Bed & Breakfast

Ashburnham

10/10 Excellent

Anonymous traveler

A well-lit garden area with a gazebo, a small house, and a large tree in the background.

Howarth House B&B

Fitchburg

10/10 Excellent

For the wedding we stayed at our very first B&B. Howarth House Bed and Breakfast in Fitchburg, Mass. It is a beautiful house built in 1910. The current owners, Sarah and Ryan purchased the house in 2020. The owners were friendly, kind, accommodating and Ryan can sure cook a great breakfast. Sarah presented us with a departing gift of her homemade Blueberry and white chocolate scones. Delicious! The room was comfortable, the location quiet and we will definitely be back. I wish I had taken more...

Darleen

A traditional white building with black shutters, a stone pathway leading to the entrance, and a signboard advertising a breakfast buffet.

Inn on Putney Road

Brattleboro

10/10 Excellent

Victoria

A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.

The Inn At Crumpin Fox

Bernardston

10/10 Excellent

I've traveled quite frequently the past several years and I can say in all honesty that this is without doubt one of the nicest places I have stayed. I was there for 2 nights and could not have asked for nicer accomodations. The room was spacious, the bed very comfortable and the bathroom spotless. The manager was very gracious, he even lent me his umbrella when it rained the day I had planned to do genealogy research in a local cemetery.

Anonymous traveler

A cozy room with a wooden staircase, a fireplace, a sofa, and a patterned rug.

The Common Man Inn & Restaurant

Claremont

10/10 Excellent

Robert

Frequently Asked Questions

How many vacation rentals are available in Cheshire County?

Expedia has plenty of vacation rentals to choose from in and around Cheshire County, so you’re guaranteed to find the right one for you.

How much is a vacation rental in Cheshire County?

The selection of Cheshire County vacation rentals we have selected for you start as low as $94 per night. Entering your travel dates in the search wizard you might find even better deals!

What type of vacation rental can I get in Cheshire County?

Vacation rentals in Cheshire County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Cheshire County vacation rentals to suit everyone.

Why should I choose a vacation rental in Cheshire County?

Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. 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.

How do I find the best deal on a vacation rental in Cheshire County?

Find vacation rentals in Cheshire County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Cheshire County.

What amenities are available in a vacation rental in Cheshire County?

The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Cheshire County vacation rentals designed to suit every budget and trip type.

When is the best time to stay in a vacation rental in Cheshire County?

Everytime is a great time to head to Cheshire County! Staying in a Cheshire County vacation rentals you will always find lots going on to keep you entertained.

Why book a vacation rental with Expedia?

Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Cheshire County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Cheshire County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Cheshire County, you can save even more.

Can I cancel my vacation rental through Expedia?

Yes, you can cancel or change your Cheshire County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.

Vacation Rentals in Cheshire County

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Upfront pricing

Top cities in Cheshire County

Keene

Check prices for these dates

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

Vikings Villages Resort

10/10 Excellent

Frequently Asked Questions

How many vacation rentals are available in Cheshire County?

How much is a vacation rental in Cheshire County?

What type of vacation rental can I get in Cheshire County?

Why should I choose a vacation rental in Cheshire County?

How do I find the best deal on a vacation rental in Cheshire County?

What amenities are available in a vacation rental in Cheshire County?

When is the best time to stay in a vacation rental in Cheshire County?

Why book a vacation rental with Expedia?

Can I cancel my vacation rental through Expedia?