Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Chesterfield holiday rentals

Interior

Holiday Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (49 reviews)
"This is a comfortable and spacious apartment in a great location central to everything in Greenfield. David is also an excellent host who communicated clearly throughout our visit. Would definitely stay here again. "
United States
Geoffrey B.
The price is HK$908
HK$1,574 total
includes taxes & fees
22 Mar - 23 Mar
Lovely 2nd Floor Apartment
Exterior

Cabin in Newfane

Wellness Getaway with a Personal Sauna, and Private River Beach!
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is HK$1,056
HK$1,954 total
includes taxes & fees
19 Mar - 20 Mar
Wellness Getaway with a Personal Sauna, and Private River Beach!
Terrace/patio

Chalet in Guilford

Vikings Villages Resort - Double Bed Room
The price is HK$1,760
HK$2,129 total
includes taxes & fees
22 Mar - 23 Mar
Vikings Villages Resort - Double Bed Room
Terrace/patio

Camping in Hinsdale

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
10.0 out of 10, Exceptional, (10 reviews)
"Yert was perfect and stocked with everything we needed,property owner showed up to make sure we had everything we needed then left us in complete privacy,location was amazing with a great scenic view."
United States
Jerry S.
The price is HK$740
HK$1,269 total
includes taxes & fees
20 Mar - 21 Mar
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Exterior

Cabin in Alstead

Owl's Nest Treehouse
10.0 out of 10, Exceptional, (19 reviews)
"We loved our stay at The Owls Nest! The location was very private, and everything was exceptionally clean. Perfect for a quick weekend getaway to relax. Would highly recommend for a couple looking to enjoy a quiet weekend. "
United States
Samantha R.
The price is HK$2,152
HK$2,632 total
includes taxes & fees
18 Mar - 19 Mar
Owl's Nest Treehouse
Outdoor spa tub

Holiday Home in Keene

Modern Downtown 12ppl Hot Tub Fire Pit Games
9.6 out of 10, Exceptional, (22 reviews)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
The price is HK$1,252
HK$2,496 total
includes taxes & fees
5 Apr - 6 Apr
Modern Downtown 12ppl Hot Tub Fire Pit Games
Private kitchen

Cabin in Brattleboro

The Studio with a View. Bring your dog, too!
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is HK$1,048
HK$2,103 total
includes taxes & fees
24 Mar - 25 Mar
The Studio with a View. Bring your dog, too!
Property grounds

Apartment in Whitingham

Lake Whitingham & Mount Snow Area Village Apartment
10.0 out of 10, Exceptional, (1 review)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is HK$1,095
HK$2,401 total
includes taxes & fees
13 Mar - 14 Mar
Lake Whitingham & Mount Snow Area Village Apartment
TV, books

Cottage in Walpole

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is HK$1,613
HK$1,979 total
includes taxes & fees
15 Mar - 16 Mar
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Interior

Apartment in Dover

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
10.0 out of 10, Exceptional, (4 reviews)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
The price is HK$665
HK$1,618 total
includes taxes & fees
31 Mar - 1 Apr
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Property grounds

Holiday Home in Putney

Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,205
HK$2,287 total
includes taxes & fees
17 Mar - 18 Mar
Family Friendly Hilltop House In Putney Vermont
Exterior

Holiday Home in Whitingham

14mi to Mt. Snow! Arcade, Private Suite, King Bed!
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is HK$1,792
HK$4,260 total
includes taxes & fees
31 Mar - 1 Apr
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Exterior

Chalet in East Dover

Chalet Mount Snow/Stratton Skiing/hiking
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$953
HK$3,462 total
includes taxes & fees
18 Mar - 19 Mar
Chalet Mount Snow/Stratton Skiing/hiking
Terrace/patio

Holiday Home in Walpole

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is HK$2,295
HK$4,723 total
includes taxes & fees
13 Mar - 14 Mar
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Fridge, microwave, oven, stovetop

Holiday Home in Colrain

Colrain Spring into Adventure HotTub AirHockey Firepit
9.8 out of 10, Exceptional, (47 reviews)
"Great house for family gatherings "
United Kingdom
John Paul B.
The price is HK$2,216
HK$5,010 total
includes taxes & fees
15 Mar - 16 Mar
Colrain Spring into Adventure HotTub AirHockey Firepit
Living area

Holiday Home in Guilford

Stunning Glass House nestled in the Vermont wilderness!
10.0 out of 10, Exceptional, (1 review)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
United States
Grant D.
The price is HK$1,648
HK$3,922 total
includes taxes & fees
8 Apr - 9 Apr
Stunning Glass House nestled in the Vermont wilderness!
Games room

Apartment in Wilmington

Luxury Unit - 101
10.0 out of 10, Exceptional, (1 review)
"It was a beautiful place and clean and updated. Plenty of room for our party of four."
United States
Michael
The price is HK$2,770
HK$4,727 total
includes taxes & fees
24 Mar - 25 Mar
Luxury Unit - 101
TV, books, stereo

Holiday Home in Dover

Secluded Vermont Chalet w/ Sweeping Mountain Views
The price is HK$1,111
HK$1,432 total
includes taxes & fees
7 Apr - 8 Apr
Secluded Vermont Chalet w/ Sweeping Mountain Views
Living area

Apartment in Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
8.0 out of 10, Very good, (2 reviews)
"The was an excellent experience all around! The place is immaculate and exactly as described, stylish and functional for our group of 8. Appreciated the fireplace, flat screens and PacMan. Check in/out instructions clear and communication w owner quick. The location was convenient for skiing Mt Snow. Jax on Tap a great spot right below for dinner and fun- our crew played shuffleboard and pool. Food was delicious! "
United States
Claudia M.
The price is HK$2,563
HK$4,649 total
includes taxes & fees
25 Mar - 26 Mar
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Fridge, microwave, oven, stovetop

Holiday Home in Keene

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
10.0 out of 10, Exceptional, (2 reviews)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
The price is HK$1,651
HK$3,896 total
includes taxes & fees
6 Apr - 7 Apr
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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 Chesterfield Hotel Reviews

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

2/10 Terrible
"I’ve been staying here for 3 yrs for a bowling tournament. Brought my kid with me expecting the pool to be fully up and serviced. No where did it ever say pool was down. Shower handle was pretty much broken and the shower head basically dribbled out. There was empty wrappers in the bathroom and hair in the tub. There was wires sticking out of a hole in the wall. Was the worst experience I’ve had there. I will not stay next year. "
Jeremy 2-night trip
Posted 5 hours ago
Best Western Plus Keene Hotel

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chesterfield!

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?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Chesterfield is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Spofford Lake. While here, Asbury United Methodist Church and Chesterfield Town Hall are other places worth a visit.

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.