Chesterfield Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Chesterfield

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

8.8 out of 10, Excellent, (49)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (30)
"Easy stay, good location for us. Would stay again. "
The price is CA $139
CA $253 total
includes taxes & fees
Jul 17 - Jul 18
Lovely 2nd Floor Apartment

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

10.0 out of 10, Exceptional, (4)
"We had a magical time at the yurt! Very sweet and rustic but comfortable. Great secluded location but close enough to restaurants and Brattleboro. We will definitely be back. "
The price is CA $178
CA $264 total
includes taxes & fees
Aug 2 - Aug 3
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

10.0 out of 10, Exceptional, (13)
"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!"
The price is CA $223
CA $349 total
includes taxes & fees
Jul 15 - Jul 16
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

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

8.4 out of 10, Very good, (29)
"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"
Bright three-level home with water views, jetted tub, firepit, and pool table

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

10.0 out of 10, Exceptional, (52)
"Would recommend if anyone wants a quiet, peaceful getaway."
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (19)
"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."
Lakefront Orange Vacation Rental - Pet Friendly!

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (38)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist

10.0 out of 10, Exceptional, (34)
"This house was the perfect family get away. My family enjoyed everything the property had to offer and also skiing close by. Amanda was very quick to respond to all my questions. Overall my family had a fantastic trip."
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (103)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

10.0 out of 10, Exceptional, (42)
"We had a wonderful stay! Perfect for two people !"
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (14)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is CA $459
CA $729 total
includes taxes & fees
Aug 7 - Aug 8
Downtown Hot Tub Escape

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (32)
"The cabin was great, beautiful surroundings. Very nice house."
Jacksonville Cabin w/ Wraparound Deck & Views

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is CA $266
CA $440 total
includes taxes & fees
Jul 14 - Jul 15
Family Friendly Hilltop House In Putney Vermont

The dreamiest place in Southern Vermont!

10.0 out of 10, Exceptional, (5)
"We enjoyed the quiet and convenience of this location to Mt. Snow. It was clean and well stocked. Host was kind and responsive."
The price is CA $424
CA $1,052 total
includes taxes & fees
Jul 17 - Jul 18
The dreamiest place in Southern Vermont!

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

10.0 out of 10, Exceptional, (2)
"We stayed here for couple of days. We loved it all! The place is lovely, very clean, spacious, big, and very convenient. The price is very reasonable. The property is beautiful overall! It has orchard trees and a lake. It reminded us the Vermont house in the movie Baby Boom. The location is very convenient too. 10 mins of driving to the MT Snow Ski Resort with lots of winter activities , and also 10 mins of driving to town center of West Dover. We walked in town and shopped in the small...
The price is CA $116
CA $282 total
includes taxes & fees
Jul 31 - Aug 1
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow

10.0 out of 10, Exceptional, (14)
"We absolutely loved the home! We couldn’t have had a better family trip! The location was great for the ski mountain. The space accommodated us nicely. We will definitely stay again if we have the chance! I highly recommend this amazing home!! "
The price is CA $694
CA $1,637 total
includes taxes & fees
Jul 15 - Jul 16
Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow

The Jelly Mill-A Peaceful River Retreat

10.0 out of 10, Exceptional, (53)
"Great location, communicative and welcoming hosts, and great amenities. We loved grilling and using the firepit. The surrounding area is great to walk around in. Easy drive from here to Mt Snow."
The Jelly Mill-A Peaceful River Retreat

Two-story, dog-friendly house with wood fireplace

8.4 out of 10, Very good, (29)
"House was awesome! Fit a large group well! Would recommend for sure!"
Two-story, dog-friendly house with wood fireplace

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"The folks are SUPER and made me feel very welome"
The price is CA $178
CA $340 total
includes taxes & fees
Jul 29 - Jul 30
Wellness Getaway with a Personal Sauna, and Private River Beach!
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.
Save an average of 15% on thousands of hotels when you're signed in

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.