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 favorite

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.

Nov 9 – 16

G$24,640 GYD per night
Guest favorite

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 6 – 13

G$23,062 GYD per night
Guest favorite

Home in Putney

4.94 out of 5 average rating, 332 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Nov 1 – 8

G$21,738 GYD 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

Superhost

Cottage in Putney

4.81 out of 5 average rating, 226 reviews

The Cottage, a house built for guests.

Mar 16 – 21

G$18,875 GYD per night
Guest favorite

Guest suite in Fitzwilliam

4.96 out of 5 average rating, 283 reviews

The Carriage House in Historic Fitzwilliam

Mar 18 – 25

G$19,422 GYD per night
Guest favorite

Barn in Chester

4.99 out of 5 average rating, 487 reviews

Inviting studio apartment above barn in Vermont

Apr 22 – 29

G$18,870 GYD per night
Guest favorite

Cottage in Bernardston

4.88 out of 5 average rating, 282 reviews

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

Sep 27 – Oct 4

G$22,819 GYD per night
Guest favorite

Barn in Marlboro

4.95 out of 5 average rating, 260 reviews

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

Nov 21 – 28

G$29,370 GYD per night
Guest favorite

Apartment in Marlboro

4.94 out of 5 average rating, 220 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Sep 5 – 12

G$30,585 GYD per night
Guest favorite

Tiny home in Brattleboro

4.95 out of 5 average rating, 173 reviews

"Mountain View" Hike In Cabin Retreat

May 9 – 16

G$19,105 GYD per night
Guest favorite

Guesthouse in Chesterfield

4.98 out of 5 average rating, 41 reviews

House on a hill

Jul 12 – 19

G$23,488 GYD per night
Guest favorite

Home in Chesterfield

4.95 out of 5 average rating, 40 reviews

The River House

May 29 – Jun 5

G$32,954 GYD per night
Superhost

Home in Chesterfield

4.92 out of 5 average rating, 84 reviews

Governer's Brook Camp - 2 Bedroom

Apr 30 – May 7

G$26,516 GYD per night
Guest favorite

Cottage in Chesterfield

5.0 out of 5 average rating, 15 reviews

Cheerful 1 bedroom cottage with lake access

Jul 22 – 29

G$37,845 GYD per night
Guest favorite

Guesthouse in Winchester

4.89 out of 5 average rating, 57 reviews

The Higgle House: A Sweetwater Farm Stay

Apr 12 – 19

G$15,099 GYD per night

Destinations to explore