Keene featuring street scenes and autumn leaves

Search Holiday Rentals in Cheshire County

Change your mind

Book hotels with free cancellation

Treat yourself

Save instantly and earn perks with One Key

Learn about One Key

Be picky

Search almost a million properties worldwide

Top Holiday Rentals in Cheshire County

Escape to a serene cabin retreat surrounded by trees and a seasonal touch.

"Besides it being a *bit* cold, our stay was great! Very close to Brattleboro and a bunch of other walkable towns. Great hiking areas. The yurt was so cute and had pretty much every cooking supply you could need. Will be back again in warmer weather! :)"

Situated in a natural setting, this cabin features a single door and a small window, surrounded by lush vegetation.

"What an absolutely charming place!! It was so lovely staying here. This place is exactly what we wanted... a little weekend escape not too far from home, nestled in the woods. Absolutely beautiful. The hosts were so kind, too!"

includes taxes & fees

20 Aug - 21 Aug

Cozy cabin interior with a central staircase, living area, and bedroom, perfect for relaxation and casual gatherings.

"We really appreciated the solitude and quiet retreat this cabin offered. "

Relax by the campfire in a serene wooded setting, surrounded by Adirondack chairs and a rustic picnic table.

"Great place just need the fire place to be fixed asap, especially for the winter time"

Relax in this inviting space with a comfortable sofa and a wooden staircase leading to an upper level.

"This was a perfect place for our family to come and relax! The cabin is a perfect size and feels so peaceful. Every comfort was provided and Tom was a great host."

Situated amidst a serene landscape, this charming house features a covered porch, a chimney, and a small front porch with a bench.

"Thank you for a peaceful weekend away in a charming cottage!"

includes taxes & fees

30 Jul - 31 Jul

Cozy cabin-style bedroom with a wood-burning stove, stone wall, and comfortable seating area.

"Had a great stay, cozy log cabin, beds were very comfortable. So nice to have a few garbage bags, paper towels, soaps and toiletries!! Also some coffee filters:) Hot tub was great too! "

Relax in this cozy cabin-style room with a comfortable sofa, coffee table, and large window offering a view of the outdoors.

"Kathleen was an amazing host and the property exceeded our expectations. The kids loved the bunk room and loft and the surrounding area provided something for all interests. We will definitely be planning another stay. "

includes taxes & fees

25 Aug - 26 Aug

"The property did not indicate this was a top floor condo. I have mobility issues and this was a real problem. There were several hairs on the bed sheets. I contacted the manager and he never responded. Washed everything myself including the mattress pad which had flakey debris on it, because we couldn’t just leave and lose our . Plus all our heavy luggage was painstakingly brought upstairs at this point. After a 5 night stay we still never heard from the Manager. This is not acceptable. ...

Relax on the covered deck amidst lush foliage and trees.

"Real Vermont feel. Pretty and nice quiet neighborhood!"

Cozy living area with a leather sofa, wooden coffee table, and staircase leading to an upper level.

"Consistently great time at this place (3rd time there)"

Relax by the serene lake with a picnic table and gazebo amidst tall pine trees.

"This place was perfect for our stay! It was clean, nicely decorated/designed and had thoughtful touches. The pictures were spot on for what to expect, it was peaceful, and the view was lovely. Crystal was great and check-in/out was easy! We would definitely stay here again."

Surrounded by lush greenery, this charming house offers a serene and secluded retreat.

"Great get away on lake Sunapee, great house just a short walk to the lake. Great place to relax and take in the sun set on the dock or grilling on the deck. Well equipped home that is super clean,just a great getaway. "

Kitchen features a central island, dining area, and window with outdoor views.

"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"

Escape to a serene lakeside retreat surrounded by lush trees and a tranquil water view.

"A very relaxing weekend getaway."

Situated in a wooded area, this cabin features a spacious porch, large windows, and a steeply pitched roof.

"Would recommend if anyone wants a quiet, peaceful getaway."

Enjoy serene views from the dock, surrounded by lush greenery and a tranquil body of water.

"We truly enjoyed the chance to escape from a busy city week and relax at Lake Sunapee on their dock, play games in the cottage, and going for a moderate hike on Mt. Kearsarge!"

"My family stayed here while in town for a family wedding. The house was very spacious and well stocked. Location was convenient for our events in Westminster. "

Enjoy cooking in this well-equipped kitchen with a refrigerator, stove, microwave, and sink.

"We loved our stay here. House was very tidy, property owner easy to communicate with, and location great right by the lake and mountain. There are also a few nice hikes nearby. "

includes taxes & fees

12 Aug - 13 Aug

Relax in a serene hot tub with breathtaking views of the surrounding snowy landscape.

"We enjoyed our stay at the Blue House. Its size and location cannot be beat when it comes to group trips. We will be back!"

Save an average of 15% on thousands of hotels when you're signed in

Top Cheshire County Hotel Reviews

Best Western Plus Keene Hotel

10/10 Excellent

"Great service and the room was great! No noise at all and quite possibly the best breakfast in a hotel I’ve ever seen!"

The Colonial Hotel

10/10 Excellent

"I reached out to this property a couple days in advance. Because I was going to be arriving quite late, and wanted to make sure that check in at that time of night was alright. I also inquired about a late check out. The property management responded to me within 24 hours and were able to to accommodate me smoothly. Very kind and friendly staff. Room was clean and spacious. I did not access this for my own needs, but I saw that there were beautiful grounds outside too- very well taken care of."

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, apart-hotels, 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 depends 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 selected for you start as low as £193 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.

Explore a world of travel with Expedia

Popular Cheshire County Cities

Marlborough Holiday Rentals

Unlock instant savings with Member Prices

Search Holiday Rentals in Cheshire County

Change your mind

Treat yourself

Be picky

Top Holiday Rentals in Cheshire County

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

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Charming Waterfront Log Cabin

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Spectacular Log Home with Private Lake Access

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Secluded Cabin w/ Private Hot Tub, Pond, Fire Pit, Free WiFi, Close to Skiing

Our pondside cabin - a charming retreat with modern amenities near Wachusett Mtn

Private NH Escape | Cozy Fireplace & Deck

Beautiful Lodging at Mount Snow with Hot Tub on Deck

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

Lakefront Orange Vacation Rental - Pet Friendly!

Charming Lake Sunapee & Mt. Sunapee Ski Cabin

Bright three-level home with water views, jetted tub, firepit, and pool table

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Lake Sunapee Cozy Cottage - Blodgett Landing

Wachusett Mountain Getaway, Lake Adjacent Home! Near 1761 Old Mill and Trails!

Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

Top Cheshire County Hotel Reviews

Best Western Plus Keene Hotel

Motel 6 Leominster, MA

Keene Elm City Hotel, Ascend Hotel Collection

Latchis Hotel

The Colonial Hotel

Doubletree by Hilton Hotel Leominster

Great Wolf Lodge Boston / Fitchburg, MA

Colonial Motel And Spa

Courtyard by Marriott Keene Downtown

Find out more about Cheshire County

Explore a world of travel with Expedia