Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Chesterfield vacation rentals

Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (53 reviews)
"Very clean, cozy and lots of nice plants! "
United States
Mary
The price is ￥18,504
￥32,064 total
includes taxes & fees
Apr 28 - Apr 29
Lovely 2nd Floor Apartment
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, (11 reviews)
"Stacy and her husband were very communicative and accommodating. We had everything we needed in the yurt and they provided us with some extra supplies as well. Would definitely stay again!"
United States
Gina M.
The price is ￥14,344
￥25,075 total
includes taxes & fees
Apr 28 - Apr 29
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
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 ￥22,313
￥41,413 total
includes taxes & fees
May 5 - May 6
Wellness Getaway with a Personal Sauna, and Private River Beach!
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is ￥35,861
￥43,369 total
includes taxes & fees
Apr 28 - Apr 29
Vikings Villages Resort - Double Bed Room
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (21 reviews)
"Great time easy to get to clean quiet and peaceful definitely would recommend for romantic getaway "
United States
Garrett B.
The price is ￥43,830
￥53,610 total
includes taxes & fees
May 5 - May 6
Owl's Nest Treehouse
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 ￥20,560
￥42,484 total
includes taxes & fees
Apr 29 - Apr 30
The Studio with a View. Bring your dog, too!
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 ￥13,547
￥32,418 total
includes taxes & fees
Apr 30 - May 1
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.2 out of 10, Wonderful, (23 reviews)
"Nice house in a nice location. "
United States
Rob B.
The price is ￥25,740
￥51,101 total
includes taxes & fees
May 3 - May 4
Modern Downtown Escape HotTub Fire Pit Games 12ppl
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 ￥22,377
￥43,449 total
includes taxes & fees
Apr 28 - Apr 29
Family Friendly Hilltop House In Putney Vermont
House (4 Bedrooms) | Interior

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
The price is ￥24,385
￥83,121 total
includes taxes & fees
Apr 28 - Apr 29
Outdoor Adventure Hub! Family Home in West Dover
4 bedrooms, travel crib, internet, bed sheets

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
West Dover
10.0 out of 10, Exceptional, (5 reviews)
"The house was just as listed. Everything we needed was there for us upon arrival. The host is amazing and was happy to welcome us in their home. We would definitely come back"
United States
Louis
The price is ￥21,835
￥86,470 total
includes taxes & fees
Apr 28 - Apr 29
Outdoor Adventure Hub! Family Home in West Dover
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 ￥31,717
￥81,220 total
includes taxes & fees
Apr 28 - Apr 29
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 ￥35,677
￥43,726 total
includes taxes & fees
Apr 28 - Apr 29
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Outdoor dining

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is ￥7,013
￥11,068 total
includes taxes & fees
May 1 - May 2
2 private mountain RV pads for rent. Full hook ups
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 ￥18,667
￥70,218 total
includes taxes & fees
May 3 - May 4
Chalet Mount Snow/Stratton Skiing/hiking
Fridge, microwave, oven, stovetop

Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
9.8 out of 10, Exceptional, (48 reviews)
"Our crew stayed here while working on a job in the area, they absolutely loved it, cleanliness was outstanding! Host provided great information about the area which was very helpful. Amenities are great! Would recommend 100% "
United States
Maureen A.
The price is ￥46,220
￥103,791 total
includes taxes & fees
May 1 - May 2
Spacious 5BR w/ Hot Tub & Games
Property grounds

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
West Dover
9.0 out of 10, Wonderful, (4 reviews)
"Clean, comfortable, our 2nd time staying here - very nice."
United States
Dan G.
The price is ￥27,892
￥91,440 total
includes taxes & fees
Apr 30 - May 1
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
Living area

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
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 ￥25,407
￥71,119 total
includes taxes & fees
May 11 - May 12
Stunning Glass House nestled in the Vermont wilderness!
Fridge, microwave, oven, stovetop

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, (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 ￥30,601
￥76,434 total
includes taxes & fees
Apr 28 - Apr 29
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
House (4 Bedrooms) | 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 ￥35,861
￥91,685 total
includes taxes & fees
Apr 28 - Apr 29
Outdoor Adventure Haven 14 Mi to Mount Snow Skiing
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"I enjoyed my stay at the Latchis very much. It was my first time there since 2018 and hope to make a return trip again very soon!"
Lawrence 1-night trip
Posted 12 hours ago
Latchis 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 vacation rental in Chesterfield?

Yes, we offer vacation rentals near top sights in Chesterfield, or you can select a more secluded option if you'd like a relaxing place to stay. Chesterfield is known for its shopping and restaurants.

What are some of the best vacation home rentals in Chesterfield?

Lovely 2nd Floor Apartment: This vacation 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 Pisgah State Park are other places worth a visit.

What are vacation rentals like in Chesterfield?

Vacation rentals are private accommodations you can stay in for several days or more in Chesterfield. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for small groups.