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Cheshire County Vacation Rentals

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Top Cities in Cheshire County

A group of hikers on rocky terrain with dense forest in the background.
Vacation RentalsVacation Rentals

Jaffrey

Jaffrey

Our top choices for Cheshire County vacation rentals

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

1. 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)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is CA $249
CA $476 total
includes taxes & fees
Sep 9 - Sep 10
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

2. 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)
"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 CA $266
CA $673 total
includes taxes & fees
Sep 8 - Sep 9
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A patio area with outdoor furniture, a small garden with purple flowers, and a white building in the background.

3. 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)
"We had a very lovely stay. "
United States
mary c.
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
A house by a lake with a dock and a boat.

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)
"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 CA $242
CA $385 total
includes taxes & fees
Sep 8 - Sep 9
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A rustic cabin with a covered porch, a small shed, and outdoor seating.

5. 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, (18 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is CA $131
CA $224 total
includes taxes & fees
Sep 21 - Sep 22
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A cabin with a dock extending into a calm river, surrounded by snow-covered trees and a clear sky.

6. 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)
"Awesome few days away great place and surroundings. Jim is always there for you ."
United States
David S.
The price is CA $309
CA $481 total
includes taxes & fees
Sep 8 - Sep 9
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
An outdoor grill area with a stone patio, a red building wall, and a view of a lake.

7. 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
Rindge
10.0 out of 10, Exceptional, (25 reviews)
"Everything was really great. Nice place...beautiful view of the lake, easy access, clean, well-equipped. "
United States
Dennis F.
The price is CA $270
CA $545 total
includes taxes & fees
Sep 8 - Sep 9
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A four-poster bed with a grey bedspread, a wooden nightstand with a lamp, a wooden dresser, and a chair.

8. 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)
"A cozy little cottage on a beautiful property. Great for 4 adults or a small family "
United States
Sheilah Z.
The price is CA $385
CA $477 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
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.

9. 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)
"This was a very cute rental in a beautiful part of New Hampshire, but it was much smaller than we imagined."
United States
Kelly
The price is CA $385
CA $477 total
includes taxes & fees
Sep 8 - Sep 9
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
A modern living room with a wooden door, a sofa, a dining table with chairs, and a mounted TV.

10. 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)
"Very nice well kept and a great location to Monadnock Hospital."
United States
Melissa M.
The price is CA $291
CA $433 total
includes taxes & fees
Sep 15 - Sep 16
Cozy Tiny House on Main Street. Fully Renovated.
Two Adirondack chairs and a fire pit in a grassy field with a forested hill in the background.

11. 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 CA $514
CA $634 total
includes taxes & fees
Sep 8 - Sep 9
Large Farmhouse with expansive views, firepit 15 min north of Keene
A kitchen with a brick fireplace, wooden cabinets, a central island with stools, and a large window with plants.

12. 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)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is CA $581
CA $992 total
includes taxes & fees
Sep 8 - Sep 9
Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region
A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

13. 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)
"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 CA $467
CA $879 total
includes taxes & fees
Sep 8 - Sep 9
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A wooden cabin with a gabled roof, multiple windows, and a front porch.

14. 2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is CA $663
CA $993 total
includes taxes & fees
Sep 8 - Sep 9
2 Cabins & Sauna on Lake Monomonac
A cabin with a covered porch, large windows, and snow-covered ground.

15. 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)
"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 CA $262
CA $426 total
includes taxes & fees
Sep 27 - Sep 28
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A lakeside park with picnic tables and a concrete walkway.

16. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is CA $76
CA $113 total
includes taxes & fees
Sep 8 - Sep 9
2 private mountain RV pads for rent. Full hook ups
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

17. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (8 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 CA $141
CA $228 total
includes taxes & fees
Sep 9 - Sep 10
Yurt Oasis in the woods of Hinsdale, NH
A modern living room with a fireplace, a mounted TV, and a leather couch.

18. 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, (25 reviews)
"I would stay here again."
United States
Ann M.
The price is CA $191
CA $318 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Cabin in a Rural Setting #16 near Temple,NH
A house entrance with a mailbox labeled '9B Mail', a wooden door, and a brick wall interior visible through the open door.

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, (43 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is CA $146
CA $265 total
includes taxes & fees
Sep 8 - Sep 9
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

20. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (64 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is CA $161
CA $278 total
includes taxes & fees
Sep 8 - Sep 9
Lovely 2nd Floor Apartment
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

Great Wolf Lodge Boston / Fitchburg, MA

Great Wolf Lodge Boston / Fitchburg, MA

8/10 Good
"Clean room, helpful staff, great amenities - only thing to improve is in the parking."
Roman 1-night trip
Posted 1 hour ago
Great Wolf Lodge Boston / Fitchburg, MA

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 $255 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.