Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite

Apartment in Putney

4.89 out of 5 average rating, 107 reviews

Hip & Cozy Storefront

Ground-level historic storefront turned into a private, hip place to sleep. Nestled in the village of Putney, VT it is just a walk to restaurants, General Store, nature trails and Next Stage Theater-short drive to Putney School, Landmark College & The Greenwood School- huge bathtub, movie screen, kitchenette with fridge, handicap accessible. Can sleep 3 or more upon request. The ski resorts of Okemo, Mt. Snow, Magic Mountain, and Stratton are not far~ making Putney a perfect ski get-a-way spot.

Aug. 4 – 11

$182 CAD per night
Guest favourite

Apartment in Dublin

4.96 out of 5 average rating, 177 reviews

Private Dublin apartment nestled in the woods

Nestled in the quiet woods just north of Mt. Monadnock our cozy one bedroom apartment invites the outdoors in with peeks of the mountain through the trees. Sit out on your private deck and enjoy the view or stroll around the yard and pick a few blueberries in season. We welcome hikers, nature lovers, those visiting friends or family or just wanting to enjoy the area's beautiful scenery and many artistic venues. I like to think of it as a peaceful sanctuary that we'd like to share with you.

Sep. 13 – 20

$171 CAD per night
Guest favourite

Guesthouse in Brattleboro

4.93 out of 5 average rating, 421 reviews

Mahalo Temple Retreat

Retreat in Mahalo's beautiful, private sound healing temple surrounded by nature, amongst streams, berry bushes, fruit & nut trees, medicinal plants and veggie gardens. We are set back just enough from a main road to find your serenity and yet close enough to civilization for human interaction and trails for hiking. Quiet and peaceful location just a few min off I-91 and just over 2 miles from the center of Brattleboro. A fun and quirky town with art cafes, restaurants, and great shops.

Jun. 17 – 24

$150 CAD per night

Popular amenities for Chesterfield vacation rentals

Stay near Chesterfield's top sights

Madame Sherri Forest26 locals recommend
Panda North Chinese And Japanese Restaurant14 locals recommend
Walker Farm22 locals recommend
Wantastiquet Mountain Natural Area13 locals recommend
Wares Grove Beach6 locals recommend
Copper Cannon Distillery3 locals recommend

Other great vacation rentals in Chesterfield

Guest favourite

Guesthouse in Brattleboro

4.99 out of 5 average rating, 197 reviews

Light Filled Loft in the Vermont Countryside

Apr. 29 – May 6

$193 CAD per night
Guest favourite

Barn in Chester

4.99 out of 5 average rating, 487 reviews

Inviting studio apartment above barn in Vermont

Apr. 29 – May 6

$148 CAD per night
Guest favourite

Home in Putney

4.94 out of 5 average rating, 332 reviews

Vermont Botanical Studio Apartment

Feb. 23 – Mar. 2

$187 CAD per night
Guest favourite

Guest suite in Fitzwilliam

4.96 out of 5 average rating, 283 reviews

The Carriage House in Historic Fitzwilliam

Jan. 17 – 24

$143 CAD per night
Guest favourite

Barn in Marlboro

4.95 out of 5 average rating, 260 reviews

The Studio With a View. Bring your dog, too!

Jan. 1 – 8

$227 CAD per night
Guest favourite

Tiny homes in Brattleboro

4.95 out of 5 average rating, 173 reviews

"Mountain View" Hike In Cabin Retreat

May 7 – 14

$144 CAD per night
Guest favourite

Apartment in Marlboro

4.94 out of 5 average rating, 220 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Feb. 2 – 9

$216 CAD per night
Guest favourite

Cottage in Bernardston

4.88 out of 5 average rating, 282 reviews

Cozy, Quiet Cottage on Country rd 2 mil from I-91

Jan. 31 – Feb. 7

$194 CAD per night
Guest favourite

Guesthouse in Chesterfield

4.98 out of 5 average rating, 41 reviews

House on a hill

May 13 – 20

$157 CAD per night
Guest favourite

Home in Chesterfield

4.95 out of 5 average rating, 40 reviews

The River House

May 18 – 25

$249 CAD per night
Superhost

Home in Chesterfield

4.92 out of 5 average rating, 84 reviews

Governer's Brook Camp - 2 Bedroom

Jun. 9 – 16

$198 CAD per night
Guest favourite

Cottage in Chesterfield

5.0 out of 5 average rating, 15 reviews

Cheerful 1 bedroom cottage with lake access

Jul. 22 – 29

$277 CAD per night

Destinations to explore