Search Holiday Rentals in Chesterfield

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May 3 - May 4
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May 4 - May 5
This weekend
May 3 - May 5

Top Holiday Rentals in Chesterfield

Interior
Charming Waterfront Log Cabin
10.0 out of 10, Exceptional, (23)
"My husband and I stayed for 2 nights at this lovely log cabin on the pond. Although the weather did not cooperate outdoors, we had all the comforts of home indoors. The cabin was warm and toasty and the view out to the pond did not disappoint-fog rising on the water in the morning, steady rain throughout the day and then clearing at night with a moon reflected on the water. The cabin is stocked with games and the tv/streaming easy to navigate. If you want peace and quiet this is the cabin to...
Charming Waterfront Log Cabin
Property grounds
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (24)
"The house was very comfortable for our family. It was well-stocked with plates, pots, and pans. Bed were comfortable."
Beautiful, private log cabin with huge, relaxing screened porch
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (32)
"Perfect litle getaway. Not to far from town, beautiful surrounding area, exactly what i was looking for."
Cozy Cottage Along Idyllic Green River
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Exterior
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
10.0 out of 10, Exceptional, (38)
"The house was very clean and cozy. Nice and peaceful get away in a remote cabin with my wife and both of the dogs! They provided dog toys and a bed for our pups with additional treats, they were very happy about this! If you are looking for a quiet get away to slow down and reconnect with your family this is the place to be!"
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Lake
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, (8)
"The house was superb for our family visit! We enjoyed it all! Linda was a perfect hostess…,so attentive!"
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Property grounds
Cozy cottage tucked away in the woods
10.0 out of 10, Exceptional, (34)
"Stayed here to celebrate a birthday, hang out with friends, and go to Stratton. The house was amazing. We really enjoyed the record player and relaxing by the wood stove. The property was kept nicely and the home was very clean. The house had all of the standard things that are typically needed. We look forward to staying there again next year."
Cozy cottage tucked away in the woods
Fridge, microwave, stovetop, coffee/tea maker
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, (22)
"This property is fairytale cute, so welcoming and relaxing. We had a beautiful stay in Vermont thanks to this location. And there were surprise puppies on site!!!!! Honestly this was the kind of trip that gives you confidence in vacation rentals. Clean, wonderfully decorated, off the beaten path a truly relaxing stay! Go outside at night!!!! We dont have stars like that in the city."
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Exterior
Dog-friendly home with a firepit, furnished deck, game room, & washer/dryer
10.0 out of 10, Exceptional, (2)
"Nice house 10 minutes from Mount Snow. Perfect for a Ski getaway. Nice Basement/Gameroom for kids and teens."
Dog-friendly home with a firepit, furnished deck, game room, & washer/dryer
Property grounds
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
10.0 out of 10, Exceptional, (11)
"Beautiful home with everything that we needed. Short drive to Landmark College to see our daughter and close to Brattleboro shopping and restaurants. The river was also wonderful to wake up to. Highly recommend! "
Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
Fridge, microwave, stovetop, coffee/tea maker
Cozy Falls Brook Cabin: Hike & Swim On-Site!
10.0 out of 10, Exceptional, (4)
"What a beautiful clean cabin nestled next to a brook with lots of hiking paths to explore. Centrally located to several ski resorts. Matt was the most excellent host! I look forward to returning during other seasons!"
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Property grounds
Lakefront Orange Vacation Rental - Pet Friendly!
10.0 out of 10, Exceptional, (6)
"Crystal was an exceptional hostess! "
Lakefront Orange Vacation Rental - Pet Friendly!
Property grounds
Spacious Dover Refuge ~ 5 Mi to Mount Snow!
10.0 out of 10, Exceptional, (9)
"Very nice property!! T"
Spacious Dover Refuge ~ 5 Mi to Mount Snow!
Fridge, microwave, oven, stovetop
Potter's Place | House in Jamaica with mountain views
10.0 out of 10, Exceptional, (2)
"The house was warm, clean, peaceful and comfortable for our short stay. We were in VT to ski at Stratton but I would love to come back in other seasons to explore the nearby state parks. I would gladly stay at this property again."
Potter's Place | House in Jamaica with mountain views
Fridge, microwave, oven, stovetop
A vacation destination in Southern Vermont
10.0 out of 10, Exceptional, (60)
"The cabin was adorable. The kitchen had everything we needed. Close to Mount Snow for us to ski. The yard was beautiful, and our pup loved it. We walked to the lake through the woods. The garage entrance was perfect for after skiing and to clean the dog after playing in the yard. It was also very clean."
A vacation destination in Southern Vermont
1 bedroom, iron/ironing board, free WiFi, bed sheets
Spectacular Mountain views with all the amentities nearby
9.8 out of 10, Exceptional, (38)
"The vrbo was as-described and the hosts exceptionally personable and friendly. Exemplary!"
Spectacular Mountain views with all the amentities nearby
Fridge, microwave, stovetop, dishwasher
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (23)
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Exterior
Family Friendly Hilltop House In Putney Vermont
9.6 out of 10, Exceptional, (50)
"The house was excellent and the view of the pond was amazing! But what we appreciated the most was Michele's help and communication about the snowstorm that was set to hit the area. She had excellent info and advice and was able to move our stay up a day so we could stay ahead of the storm. We had a great trip to Vermont and very much appreciate her help!"
The price is £249
includes taxes & fees
7 May - 8 May
Family Friendly Hilltop House In Putney Vermont
Property grounds
Rustic Retreat: Cozy Log Cabin
9.6 out of 10, Exceptional, (4)
"The cabin is very nice. It is in good shape. It is well decorated. It is very comfy, and it has everything you could possibly need. It is very close to the town of Wilmington, hiking trails, fishing, pond, lakes, and rivers. Sarah, the owner, was very responsive to any questions or needs. There’s a very nice eclectic restaurant in Wilmington that we really enjoyed called Jezebel. There is a high likelihood we would be coming back at some point in the future."
Rustic Retreat: Cozy Log Cabin
Exterior
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, (34)
"Linda was wonderful in her review of the property and was very accommodating in all aspects of our stay. The cottage was well equipped and very comfortable including the mattress. We enjoyed the lake and a little fishing. The area is very nice and we did some exploring. It was very quiet and we rarely even saw anyone while we were on the lake. We hope to return in the spring or summer. Many thanks to Linda and Brad"
Waterfront Cottage on Scenic Sportsman Pond
Terrace/patio
Beautiful Mt area with beautiful scenic views; 6 miles to Mount Snow Ski Resort.
9.4 out of 10, Exceptional, (10)
"We loved our stay and would definitely come back."
Beautiful Mt area with beautiful scenic views; 6 miles to Mount Snow Ski Resort.
Don't see what you're looking for?
See all available properties in Chesterfield
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.

Chesterfield Holiday Rental Travel Info

Number of holiday rentals
3
Known landmarks
Pisgah State Park, Actors Theatre Playhouse and Spofford Lake
International airports
Boston, MA (BOS-Logan Intl.) and Manchester, NH (MHT-Manchester-Boston Regional)

Other types of properties in Chesterfield you may be interested in

Hypo-allergenic bedding, in-room safe, desk, laptop workspace
Courtyard by Marriott Keene Downtown
3.0 star property
8.8 out of 10, Excellent, (895)
"Cleanest hotel bathroom I've ever seen. Good food. Friendly staff. "
The price is £110
includes taxes & fees
20 May - 21 May
Courtyard by Marriott Keene Downtown
Lobby
Hampton Inn Brattleboro
2.5 star property
8.4 out of 10, Very good, (894)
"Good stay "
The price is £114
includes taxes & fees
21 May - 22 May
Hampton Inn Brattleboro
Concierge desk
The Covered Bridge Inn
2.5 star property
8.2 out of 10, Very good, (1003)
"Plenty of restaurants, very clean and updated rooms."
The price is £78
includes taxes & fees
3 Jun - 4 Jun
The Covered Bridge Inn
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.

Everything you need to know about Chesterfield 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 Chesterfield 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 Chesterfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. 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 Chesterfield 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 Chesterfield holiday rentals we have selected for you start as low as £249 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield 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 Chesterfield 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 Chesterfield 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 Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay. Chesterfield is known for its shopping and restaurants.

What are some of the best holiday rentals that Chesterfield has to offer?

Charming Waterfront Log Cabin: This holiday home rental outside of Chesterfield is located on the waterfront, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What can I see and do in Chesterfield?

Explore the area and family-friendly sights such as Brattleboro Bowl, or get out into nature at a spot like Pisgah State Park. Asbury United Methodist Church and Spofford Lake are a couple of places you'll find in the wider area.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals offer amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for families.

Recent reviews of Chesterfield properties
Expedia verified reviews

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

5/5 Excellent
"The room was comfortable and clean. Breakfast was great "
A verified traveller stayed at Hampton Inn & Suites Keene
Posted 4 days ago
Hampton Inn & Suites Keene