A large rock with carved faces and a river in the background.

Cheshire County 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.

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, (19 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is AU$232
includes taxes & fees
1 Oct - 2 Oct
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A lakeside park with picnic tables and a concrete walkway.

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

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is AU$117
includes taxes & fees
25 Sept - 26 Sept
2 private mountain RV pads for rent. Full hook ups
A two-story house with a front porch, a staircase, and a small garden area.

3. Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
9.6 out of 10, Exceptional, (7 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
The price is AU$280
includes taxes & fees
4 Oct - 5 Oct
Central Large 2-bedrooms with office in Keene
An outdoor grill area with a stone patio, a red building wall, and a view of a lake.

4. 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 AU$545
includes taxes & fees
14 Oct - 15 Oct
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

5. 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 AU$664
includes taxes & fees
20 Oct - 21 Oct
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A house by a lake with a dock and a boat.

6. 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)
"Amazing place. We really enjoyed our brief stay. Great host. "
United States
Gary S.
The price is AU$405
includes taxes & fees
27 Sept - 28 Sept
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A cabin with a dock extending into a calm river, surrounded by snow-covered trees and a clear sky.

7. 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 AU$528
includes taxes & fees
6 Oct - 7 Oct
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

8. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (26 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is AU$553
includes taxes & fees
25 Oct - 26 Oct
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

9. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
Fitzwilliam
10.0 out of 10, Exceptional, (1 review)
"This place was really beautifully appointed and thoughtfully stocked. Kitchen stock was great.Lots of coffees, teas, bottled water…all very thoughtful touches. Comfy beds. Beautiful little home. Pond was really nice. Convenient to Monandock. Really loved it. Lots of appreciation for the hosts."
United States
Len S.
The price is AU$412
includes taxes & fees
25 Sept - 26 Sept
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
A cabin with a covered porch, large windows, and snow-covered ground.

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)
"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 AU$437
includes taxes & fees
18 Oct - 19 Oct
Cabin & Sauna on Lake Monomonac near Mt. Monadnock
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

11. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.4 out of 10, Exceptional, (10 reviews)
"What an amazing Yurt. The location was so peaceful. The yurt and outhouse was super clean. Hosts were friendly and helpful. I would stay again if in the area."
United States
Troy H.
The price is AU$207
includes taxes & fees
28 Sept - 29 Sept
Yurt Oasis in the woods of Hinsdale, NH
A patio area with outdoor furniture, a small garden with purple flowers, and a white building in the background.

12. 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.
The price is AU$865
includes taxes & fees
8 Oct - 9 Oct
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.

13. Cobb Meadow House: Cozy 5 Bedroom Retreat

Cobb Meadow House: Cozy 5 Bedroom Retreat
Dublin
10.0 out of 10, Exceptional, (26 reviews)
"Good place to stay during a wedding week"
United States
Veronique S.
The price is AU$999
includes taxes & fees
27 Sept - 28 Sept
Cobb Meadow House: Cozy 5 Bedroom Retreat
A house with a deck and a dock extending into a pond, surrounded by autumn foliage.

14. 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 AU$895
includes taxes & fees
26 Sept - 27 Sept
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
A wooden cabin with a gabled roof, multiple windows, and a front porch.

15. 2 Cabins & Sauna on Lake Monomonac

2 Cabins & Sauna on Lake Monomonac
Rindge
The price is AU$1,188
includes taxes & fees
5 Oct - 6 Oct
2 Cabins & Sauna on Lake Monomonac
A modern living room with a wooden door, a sofa, a dining table with chairs, and a mounted TV.

16. 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.
Cozy Tiny House on Main Street. Fully Renovated.
A small, single-story house with a front door open, revealing a kitchen area with a sink and cabinets.

17. 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, (23 reviews)
"Amazing best place in nh"
United States
Dean S.
The price is AU$262
includes taxes & fees
27 Sept - 28 Sept
Cozy Cabin in a rural setting #12 in Temple 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 AU$307
includes taxes & fees
25 Sept - 26 Sept
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
9.8 out of 10, Exceptional, (44 reviews)
"Wonderful stay! Amazing location!"
United States
Basmattee B.
The price is AU$305
includes taxes & fees
5 Oct - 6 Oct
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
A stone pathway leading to a large, multi-story building surrounded by trees and shrubs.

20. Cottage beside a waterfall

Cottage beside a waterfall
Wilton
10.0 out of 10, Exceptional, (22 reviews)
"Unique artist's cottage, curated with great care and humor. Amazing property with an actual waterfall behind the cottage. Nice covered porch to view the scene. Excellent bed."
United States
Patrick B.
The price is AU$405
includes taxes & fees
25 Sept - 26 Sept
Cottage beside a waterfall
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

10/10 Excellent
"convenient and safe place to stay while on a drivng vacation through New England"
CHERYL 1-night trip
Posted 6 hours ago
Days Inn by Wyndham Keene NH

Find out more about Cheshire County

Everything you need to know about Cheshire County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire County holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cheshire County holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheshire County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Cheshire County holiday rentals we have chosen for you start as low as AU$262 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 holiday 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 holiday.

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.