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, (45)
"A great little cabin close to Mt. Snow. Accurate description. Fire place didn’t work. Would stay here again. "
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (14)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (113)
"Great place to stay with friends and family. Will be visiting again!"
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

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

10.0 out of 10, Exceptional, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Spectacular 4 Season Home on Spruce Lake

9.8 out of 10, Exceptional, (65)
"The place and location are gorgeous, we absolutely loved it."
Spectacular 4 Season Home on Spruce Lake

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (12)
"Very cozy basement apartment overlooking the water. Quiet road. Owner was very pleasant and accommodating."
Lakefront Orange Vacation Rental - Pet Friendly!

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

9.4 out of 10, Exceptional, (15)
"We had a fun time enjoying the view and playing board games plus outdoor pursuits. Thanks for sharing your home."
Rustic, dog-friendly escape with private pool, sweeping views, & W/D

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (44)
"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 River Retreat

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

8.4 out of 10, Very good, (25)
"We stayed three nights here. Just the two of us. I felt the pictures were misleading. Much smaller than expected. Since it was just the two of us it was perfect. "
Bright three-level home with water views, jetted tub, firepit, and pool table

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

9.8 out of 10, Exceptional, (8)
"Great host"
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

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

10.0 out of 10, Exceptional, (51)
"Would recommend if anyone wants a quiet, peaceful getaway."
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Spectacular Mountain views with all the amentities nearby

9.8 out of 10, Exceptional, (51)
"What a wonderful place to stay!! We were in town for my 50th high school reunion, hadn’t been back to the area in 35 years. Our accommodations enhanced a beautiful weekend, and the foliage was the cherry on top! Spacious, clean, tastefully furnished and decorated. Well equipped with every utensil, and kitchen appliance you could need! Comfy bed, great shower & good water pressure too! Secluded and quiet, but very convenient to Bernardston, Northfield and Greenfield as well as I-91. Highly...
Spectacular Mountain views with all the amentities nearby

New-Lakehouse w/Hot Tub. Min from town and Skiing

6.0 out of 10, (1)
"The listing was updated between the time I booked and my arrival (it’s presently accurate) so we were disappointed to discover they were suddenly calling a pull out couch “a bedroom”. We made it work but it wasn’t what we were expecting. When we called Emilio to sort it out, he was very responsive and sent someone over who was SO helpful in getting linens sorted out and even lighting the grill for us. The house itself is just ok. Felt like a cheap remodel - nails poking out of door trim in an...
New-Lakehouse w/Hot Tub. Min from town and Skiing

Beautiful Townhouse In Turners Falls!

9.8 out of 10, Exceptional, (128)
"I had a Great Stay, nice place."
Beautiful Townhouse In Turners Falls!

Two-story, dog-friendly house with wood fireplace

8.6 out of 10, Excellent, (28)
"House was awesome! Fit a large group well! Would recommend for sure!"
Two-story, dog-friendly house with wood fireplace

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

9.8 out of 10, Exceptional, (10)
"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "
The price is AU$770
includes taxes & fees
4 Mar - 5 Mar
14mi to Mt. Snow! Arcade, Private Suite, King Bed!

Potter's Place | House in Jamaica with mountain views

9.6 out of 10, Exceptional, (4)
"Stayed at this lovely home for a short weekend trip in the winter. Very convenient location, clean and well kept. Be sure to have AWD and proper tires if you visit in the winter!"
Potter's Place | House in Jamaica with mountain views

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

10.0 out of 10, Exceptional, (33)
"We had another great stay for us at the Fiddler's rest. The cabin is beautifully set in a private stetting in the forest. The interior design is colorful and tasteful. The cabin could comfortable host or group of 4 people. The internet connection was great. We would be happy to visit again!"
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

Cozy Log Cabin on the River | Fireplace | Loft

10.0 out of 10, Exceptional, (9)
"Super nice, cozy cabin with all the necessary kitchen tools. Keurig pods and creamer pods in the fridge were a really nice touch! Bed was comfy and shower was great too. Pet friendly is also a great bonus! "
Cozy Log Cabin on the River | Fireplace | Loft

Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow

10.0 out of 10, Exceptional, (12)
"Great house for groups or a big family. Lots of games/arcade/ping pong. Hot tub jazuzzi tub in the master bedroom were so nice to have.It was an investment, but was worth it to be able to have the whole family comfortably. "
Beautiful Lakefront Log Cabin 15 Minutes from Mount Snow
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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Other types of properties in Chesterfield you may be interested in

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1000)
"All ok everything worked well just older decor "
The price is AU$189
includes taxes & fees
20 Feb - 21 Feb
Colonial Motel And Spa

Comfort Inn & Suites Brattleboro I-91

2.5 star property
8.6 out of 10, Excellent, (588)
"Convenient to skiing mountains"
The price is AU$184
includes taxes & fees
3 Mar - 4 Mar
Comfort Inn & Suites Brattleboro I-91

The Putney Inn

2.5 star property
8.4 out of 10, Very good, (1002)
"Liked the convenience of easy-on, and easy off I-91. The room was spacious and comfortable. Bathroom was clean and fixtures were like new. Comfortable bed. Breakfast was forgettable. Nothing fancy. But they did have hot waffles. All the staff were helpful and friendly. This is a no-frills roadside motel priced affordably. Glad I stayed at the Putney Inn. "
The price is AU$160
includes taxes & fees
26 Feb - 27 Feb
The Putney Inn
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.

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?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This holiday home rental outside of Chesterfield is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Pisgah State Park. Asbury United Methodist Church and Spofford Lake are a couple of places you'll find in the wider area.

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.