Chesterfield Vacation Rentals from ￥12,490: Search Short-Term Rentals

Q: 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.

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Vacation Rentals in Chesterfield

Our top choices for Chesterfield vacation rentals

"This comfortable 2-bedroom house on a tranquil NH pond was the perfect weekend escape! We absolutely loved the peaceful setting and beautiful views. It was incredibly relaxing and exactly what we needed. Highly recommend!"

"Treehouse was just as the pictures and description portray. It was clean, quiet and peaceful. My wife and I stayed at the Owl's Nest Treehouse for just a quick one night get away. It was the perfect spot for some quiet time alone and a soak in the hot tub. The check in process was as simple as it gets, and the owners were very responsive to the few questions we asked. For dinner we went to Springfield VT (about a 30 min drive). You can probably find something a little closer, but Alstead...

￥49,425 total

includes taxes & fees

Sep 7 - Sep 8

"a fantastic weekend getaway in the mountains! quiet neighborhood with stunning night time views of the stars. such a cozy cabin, very clean, linens provided, nice property with a little fire pit too! very friendly host, easy to contact and pleasant. "

"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "

￥29,720 total

includes taxes & fees

Aug 27 - Aug 28

"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "

￥61,221 total

includes taxes & fees

Aug 27 - Aug 28

"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! :)"

"really enjoyed our stay. Place would be much better if there was a microwave."

"Was in town for a race with friends. Great base camp for before and after on an amazing property "

Smart TV, fireplace, DVD player, table tennis

"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"

"We had so much fun between swimming and having a fire . The place is beautiful and private and yet not to far from everything."

"The property was beautiful--great views, super peaceful, and fabulous hosts. "

￥49,042 total

includes taxes & fees

Sep 23 - Sep 24

Fridge, microwave, stovetop, coffee/tea maker

"A dream Vt. property, peaceful and scenic, with no worries"

"The folks are SUPER and made me feel very welome"

￥37,358 total

includes taxes & fees

Sep 1 - Sep 2

"There was a little problem with the lockbox, but Catherine was available to help solve it. We were staying in the house instead of the “cozy apartment.” Except for a somewhat difficult staircase and a couple of doors to the deck that did not have screens, we have no complaints. They location was beautiful, but a bit of a distance from places we wanted to go to. The price was very fair, and I would recommend this location to others."

￥30,220 total

includes taxes & fees

Aug 30 - Aug 31

3 bedrooms, travel crib, free WiFi, bed sheets

"We really appreciated the solitude and quiet retreat this cabin offered. "

"The house was great and offered amazing views of the VT mountains! Definitely recommend it and will be back!"

"Loved the area"

￥32,700 total

includes taxes & fees

Sep 9 - Sep 10

"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"

"We had a great experience at Erika’s place. The house was great. Spacious & cozy at the same time. Plenty of amenities to keep the kids entertained from the theater in the basement to card games, fussball, darts, backyard, and firepit,for roasting marshmallows. We hiked at Molly Stark, went to the reservoir, & skied at Mt. Snow all in under 20 min away. We had a good time, it was a perfect getaway for our spring break. "

"Would recommend if anyone wants a quiet, peaceful getaway."

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Top Chesterfield Hotel Reviews

Riverside Hotel, Ascend Hotel Collection

10/10 Excellent

"Great place!"

Keene Elm City Hotel, Ascend Hotel Collection

10/10 Excellent

"Great experience but our only issue was that the sink was outside of the bathroom in the sleeping area other than that I would definitely recommend this hotel and stay again. The hotel was spotless and the breakfast was very good for what we paid for the room, 9 out of 10 just because of the wash hand basin location. "

Vikings Villages Resort

10/10 Excellent

"Our stay at Vikings Villages was fantastic. The cottages are done very tastefully, have everything you need and are very clean. The grounds are beautiful, there's a nice firepit to enjoy in the evening. We loved watching the sheep also. The owner was very friendly and helpful with restaurant suggestions. We'll definitely be back for a longer stay in the future. "

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

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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.

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Chesterfield Vacation Rentals

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Vacation Rentals in Chesterfield

Our top choices for Chesterfield vacation rentals

Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Owl's Nest Treehouse

Cozy Updated Log Cabin with Mountain Views close to Monadnock

Lovely 2nd Floor Apartment

Downtown Hot Tub Escape

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

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

Jacksonville Cabin w/ Wraparound Deck & Views

Beautiful Custom Built Timber Frame Home, Sleeps 11

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

Family Friendly Hilltop House In Putney Vermont

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

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

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Charming Waterfront Log Cabin

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

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

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

Lakes and Hiking Summertime - Spacious 4-bedroom Pet Friendly Home

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

Top Chesterfield Hotel Reviews

Riverside Hotel, Ascend Hotel Collection

The Covered Bridge Inn

Keene Elm City Hotel, Ascend Hotel Collection

Vikings Villages Resort

Hampton Inn Brattleboro

Comfort Inn & Suites Brattleboro I-91

Best Western Plus Keene Hotel

The Putney Inn

Colonial Motel And Spa

Find out more about Chesterfield

Frequently asked questions