Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Chesterfield holiday rentals

Terrace/patio

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, (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$705
HK$1,232 total
includes taxes & fees
28 Mar - 29 Mar
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
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$666
HK$1,620 total
includes taxes & fees
9 Apr - 10 Apr
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (50 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$909
HK$1,576 total
includes taxes & fees
1 Apr - 2 Apr
Lovely 2nd Floor Apartment
Exterior

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
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$1,058
HK$2,009 total
includes taxes & fees
30 Mar - 31 Mar
Wellness Getaway with a Personal Sauna, and Private River Beach!
Exterior

Central Large 2-bedrooms with office in Keene

Central Large 2-bedrooms with office in Keene
Keene
10.0 out of 10, Exceptional, (2 reviews)
"Friendly hosts and excellent location to walk to downtown."
United States
Joshua
The price is HK$846
HK$1,088 total
includes taxes & fees
6 Apr - 7 Apr
Central Large 2-bedrooms with office in Keene
Fridge, microwave, oven, stovetop

Colrain Spring into Adventure HotTub AirHockey Firepit

Colrain Spring into Adventure HotTub AirHockey Firepit
Colrain
9.8 out of 10, Exceptional, (48 reviews)
"Great house for family gatherings "
United Kingdom
John Paul B.
The price is HK$2,219
HK$4,999 total
includes taxes & fees
25 Mar - 26 Mar
Colrain Spring into Adventure HotTub AirHockey Firepit
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
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$1,199
HK$2,220 total
includes taxes & fees
7 Apr - 8 Apr
Family Friendly Hilltop House In Putney Vermont
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
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$945
HK$3,341 total
includes taxes & fees
13 Apr - 14 Apr
Chalet Mount Snow/Stratton Skiing/hiking
Private kitchen

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
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$1,042
HK$2,088 total
includes taxes & fees
13 Apr - 14 Apr
The Studio with a View. Bring your dog, too!
Interior

Outdoor Adventure Haven 14 Mi to Mount Snow Skiing

Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
3.0 star property
Newfane
The price is HK$1,762
HK$4,506 total
includes taxes & fees
15 Apr - 16 Apr
Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
Property grounds

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
Whitingham
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$1,097
HK$2,395 total
includes taxes & fees
29 Mar - 30 Mar
Lake Whitingham & Mount Snow Area Village Apartment
Outdoor spa tub

Modern Downtown 12ppl Hot Tub Fire Pit Games

Modern Downtown 12ppl Hot Tub Fire Pit Games
Keene
9.6 out of 10, Exceptional, (22 reviews)
"Nice house in a nice location. "
United States
Rob B.
The price is HK$1,132
HK$2,333 total
includes taxes & fees
29 Mar - 30 Mar
Modern Downtown 12ppl Hot Tub Fire Pit Games
TV, books, stereo

Secluded Vermont Chalet w/ Sweeping Mountain Views

Secluded Vermont Chalet w/ Sweeping Mountain Views
Dover
The price is HK$1,112
HK$4,026 total
includes taxes & fees
25 Mar - 26 Mar
Secluded Vermont Chalet w/ Sweeping Mountain Views
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is HK$1,762
HK$2,193 total
includes taxes & fees
25 Mar - 26 Mar
Vikings Villages Resort - Double Bed Room
Terrace/patio

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, (51 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is HK$2,256
HK$4,657 total
includes taxes & fees
30 Mar - 31 Mar
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
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$2,154
HK$2,626 total
includes taxes & fees
29 Mar - 30 Mar
Owl's Nest Treehouse
Property grounds

Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
The price is HK$811
HK$1,305 total
includes taxes & fees
6 Apr - 7 Apr
Yurt Oasis in the woods of Hinsdale, NH
Living area

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
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$2,566
HK$4,620 total
includes taxes & fees
7 Apr - 8 Apr
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Exterior

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

14mi to Mt. Snow! Arcade, Private Suite, King Bed!
Whitingham
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$1,606
HK$3,886 total
includes taxes & fees
2 Apr - 3 Apr
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
TV, books

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
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is HK$1,704
HK$2,036 total
includes taxes & fees
31 Mar - 1 Apr
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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

8/10 Good
"Room was fine. Only stayed one night for a quick trip. Didn't realize that the restaurant was closed on Sundays. Was looking for a meal after a long drive, but there were plenty of places to eat in the area. "
Paul 1-night trip
Posted 3 hours ago
Best Western Plus Keene Hotel

Find out more about Chesterfield

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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?

Lovely 2nd Floor Apartment: This holiday home rental outside of Chesterfield offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.