Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

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

8.8 out of 10, Excellent, (47)
"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, (26)
"Easy stay, good location for us. Would stay again. "
The price is NZ$301
includes taxes & fees
2 July - 3 July
Lovely 2nd Floor Apartment

Downtown Hot Tub Escape

9.2 out of 10, Wonderful, (14)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is NZ$658
includes taxes & fees
29 June - 30 June
Downtown Hot Tub Escape

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 NZ$354
includes taxes & fees
29 June - 30 June
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

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

The Jelly Mill-A Peaceful River Retreat

10.0 out of 10, Exceptional, (52)
"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

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 NZ$1,248
includes taxes & fees
6 July - 7 July
The dreamiest place in Southern Vermont!

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

Hike & Swim On-Site: Cozy Falls Brook Cabin

10.0 out of 10, Exceptional, (10)
"Great little cabin, would definitely stay again!"
Hike & Swim On-Site: Cozy Falls Brook Cabin

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 NZ$342
includes taxes & fees
30 June - 1 July
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

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 NZ$334
includes taxes & fees
29 June - 30 June
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (55)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is NZ$562
includes taxes & fees
29 June - 30 June
Family Friendly Hilltop House In Putney Vermont

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (17)
"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!

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 NZ$405
includes taxes & fees
2 July - 3 July
Wellness Getaway with a Personal Sauna, and Private River Beach!

Beautiful Townhouse In Turners Falls!

9.8 out of 10, Exceptional, (135)
"A terrific, cozy place, convenient, in a cute neighborhood -- super easy check in --- clear directions --- couldn't ask for anything more."
Beautiful Townhouse In Turners Falls!

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (53)
"We had so much fun between swimming and having a fire . The place is beautiful and private and yet not to far from everything."
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

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

Western Mass Getaway-Airhockey-Hot tub-Firepit

9.8 out of 10, Exceptional, (36)
"Great place and convenient to get to and from Berkshire East."
The price is NZ$1,404
includes taxes & fees
5 July - 6 July
Western Mass Getaway-Airhockey-Hot tub-Firepit

Rustic, dog-friendly escape with private pool, sweeping views, & W/D

9.4 out of 10, Exceptional, (15)
"The house was great and offered amazing views of the VT mountains! Definitely recommend it and will be back!"
Rustic, dog-friendly escape with private pool, sweeping views, & W/D

Timber frame home with A/C

2.0 star property
10.0 out of 10, Exceptional, (1)
"Enjoyed this place "
Timber frame home with A/C
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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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?

The Jelly Mill-A Peaceful River Retreat: This holiday home rental outside of Chesterfield is located on a river, and has a patio, a garden and a BBQ 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. Make the most of games in this rental home to help you unwind.

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.