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Holiday rentals in Chesterfield

Find and book unique accommodation on Airbnb

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Popular amenities for Chesterfield holiday rentals

Stay near Chesterfield's top sights

Whetstone Station Restaurant and Brewery113 locals recommend
Brattleboro Food Co-Op102 locals recommend
Latchis Theatre60 locals recommend
Amy's Bakery Arts Cafe53 locals recommend
Brattleboro Museum & Art Center53 locals recommend
Peter Havens Restaurant51 locals recommend

Other great holiday rentals in Chesterfield

Guest favourite
Home in Bellows falls
5 out of 5 average rating, 9 reviews

Amazing Views, Skiing Nearby and Amenities Galore!

GillianRating, 5 stars2 months ago
We absolutely loved our stay at Barbara’s home! It was spacious enough to accommodate 6 adults and 1 child with no issue. The kitchen is well appointed, allowing us to cook meals throughout our stay. We had a small storm roll through, which dropped 5” of snow overnight (great for our next day on the mountain!), and we were thrilled to see that the driveway and walkway had been cleared prior to 7am. The bedrooms were comfortable and the view from the great room is truly stunning. Would love to stay here again! Thank you, Barbara!
Top guest favourite
Holiday home in Tilton
5 out of 5 average rating, 49 reviews

Cheerful 4 bedroom, lake-front vacation home

JoanRating, 5 stars1 month ago
The house is clean, very easy to access, ample parking space, it actually is more beautiful than how it looks in the photos
Superhost
Home in Manchester
4.86 out of 5 average rating, 35 reviews

Your VT Dream House: Fireplace, Pool, Dogs

AtulRating, 5 stars8 months ago
Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.
Superhost
Cabin in Bridgewater
4.91 out of 5 average rating, 100 reviews

100 Acres Views & Creek near Woodstock/Killington

ChristopherRating, 5 stars1 month ago
Had a great stay with friends at Laura’s place. Laura was friendly flexible and reached out to make sure we didn’t have any issues checking in. Very nice place with a nice Vermont feel. 10-15 minutes from skyeship base. Had a great weekend. Would stay again.
Guest favourite
Home in Wilmington
4.88 out of 5 average rating, 105 reviews

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

JamesRating, 5 stars2 weeks ago
Place was great! Less than 10 minutes to Mount Snow. We had fun playing ping-pong, air hokey, pool, and darts! Relaxed by the wood burning stove. Lots of rooms and beds.
Top guest favourite
Home in Plymouth
5 out of 5 average rating, 16 reviews

Luxury Modern Cabin near Okemo & Killington

TariQRating, 5 stars1 month ago
Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!
Guest favourite
Home in Enfield
4.95 out of 5 average rating, 19 reviews

Upper Valley Shaker-Style Home, close to Dartmouth

ScottRating, 5 stars6 months ago
Barbara's place is a real gem. So clean, with a beautiful mix of antique and woodsy modern furniture, and a wonderfully comfortable living area overlooking a meandering brook which a few hundred yards down the road leads to the lake. The kitchen was well-equipped and modern, and beddings and beds were very comfortable. While the house was close too a busy road, we didn't hear a thing, and for summer users the deck is completely away from the road, overlooking the brook. Even more than we expected.
Superhost
Tiny home in Fort Edward
4.86 out of 5 average rating, 58 reviews

Tiny Home In Paradise “The Big Dipper”

AlannaRating, 5 stars10 months ago
If you’re looking for a quiet place to get away for the weekend, look no further!! Pete was so nice and incredibly responsive. My fiancée and I will definitely be staying here again!

Destinations to explore