Holiday Rentals in Chesterfield

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Holiday Rentals in Chesterfield

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

10.0 out of 10, Exceptional, (4)
"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!"
The price is €257
includes taxes & fees
3 Sept - 4 Sept
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Owl's Nest Treehouse

10.0 out of 10, Exceptional, (7)
"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...
The price is €296
includes taxes & fees
24 Aug - 25 Aug
Owl's Nest Treehouse

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.4 out of 10, Exceptional, (25)
"Very nice, clean, and great area. We enjoyed it very much!"
Cozy Updated Log Cabin with Mountain Views close to Monadnock

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

Downtown Hot Tub Escape

9.6 out of 10, Exceptional, (17)
"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "
The price is €442
includes taxes & fees
24 Aug - 25 Aug
Downtown Hot Tub Escape

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (32)
"Easy stay, good location for us. Would stay again. "
The price is €178
includes taxes & fees
24 Aug - 25 Aug
Lovely 2nd Floor Apartment

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (33)
"Was in town for a race with friends. Great base camp for before and after on an amazing property "
Jacksonville Cabin w/ Wraparound Deck & Views

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (106)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11

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

8.6 out of 10, Excellent, (56)
"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

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

10.0 out of 10, Exceptional, (55)
"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

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 €252
includes taxes & fees
6 Sept - 7 Sept
Family Friendly Hilltop House In Putney Vermont

Charming Waterfront Log Cabin

9.4 out of 10, Exceptional, (40)
"We really appreciated the solitude and quiet retreat this cabin offered. "
Charming Waterfront Log Cabin

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 €215
includes taxes & fees
10 Sept - 11 Sept
Wellness Getaway with a Personal Sauna, and Private River Beach!

Deck, Mountain Views: Colorful Retreat in Vernon!

10.0 out of 10, Exceptional, (2)
"comfortable and quiet... would stay again! (you must be comfortable with stairs though)"
Deck, Mountain Views: Colorful Retreat in Vernon!

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

10.0 out of 10, Exceptional, (3)
"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."
The price is €181
includes taxes & fees
31 Aug - 1 Sept
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

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

10.0 out of 10, Exceptional, (45)
"A dream Vt. property, peaceful and scenic, with no worries"
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

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

9.2 out of 10, Wonderful, (17)
"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

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 €195
includes taxes & fees
9 Sept - 10 Sept
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Lakefront Orange Vacation Rental - Pet Friendly!

10.0 out of 10, Exceptional, (23)
"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, (31)
"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
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.