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Top Holiday Rentals in Chesterfield

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

8.8 out of 10, Excellent, (53)
"Great place just need the fire place to be fixed asap, especially for the winter time"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (31)
"Easy stay, good location for us. Would stay again. "
The price is £155
includes taxes & fees
4 Aug - 5 Aug
Lovely 2nd Floor Apartment

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

10.0 out of 10, Exceptional, (5)
"Besides it being a *bit* cold, our stay was great! Very close to Brattleboro and a bunch of other walkable towns. Great hiking areas. The yurt was so cute and had pretty much every cooking supply you could need. Will be back again in warmer weather! :)"
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 £196
includes taxes & fees
20 Aug - 21 Aug
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (22)
"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!

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, (53)
"Would recommend if anyone wants a quiet, peaceful getaway."
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (39)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

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

10.0 out of 10, Exceptional, (44)
"Our stay at Fiddlers Rest was PERFECT! It was a great cozy getaway for our family and dog. The accommodations were excellent and the host did a wonderful job providing everything that was needed for a wonderful weekend getaway. We definitely will be coming back! "
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

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

10.0 out of 10, Exceptional, (34)
"Absolutely gorgeous mountain view, beautiful cabin, fully stocked kitchen, loved the hiking trails! Owners thought of every little detail to make it feel like home away from home. "
Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (15)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is £372
includes taxes & fees
4 Aug - 5 Aug
Downtown Hot Tub Escape

Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

10.0 out of 10, Exceptional, (5)
"In town for funeral, the place was great. Very roomy and comfy."
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

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 £189
includes taxes & fees
6 Aug - 7 Aug
Wellness Getaway with a Personal Sauna, and Private River Beach!

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

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 £222
includes taxes & fees
18 Aug - 19 Aug
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 £593
includes taxes & fees
4 Aug - 5 Aug
The dreamiest place in Southern Vermont!

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

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 £159
includes taxes & fees
7 Aug - 8 Aug
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

The Jelly Mill-A Peaceful River Retreat

10.0 out of 10, Exceptional, (56)
"Very much off the beaten path, but lets you experience the beauty of Vermont. Quiet and peaceful. A beautiful little property that served our needs perfectly. Would definitely come back."
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
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

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 Pisgah State Park 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.