Some info has been automatically translated. Show original language

Holiday rentals in Chesterfield

Find and book unique accommodation on Airbnb

When results are available, navigate with the up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages

Popular amenities for Chesterfield holiday rentals

Stay near Chesterfield's top sights

Whetstone Station Restaurant and Brewery114 locals recommend
Brattleboro Food Co-Op102 locals recommend
Latchis Theatre60 locals recommend
The Marina59 locals recommend
Amy's Bakery Arts Cafe53 locals recommend
Brattleboro Museum & Art Center53 locals recommend

Other great holiday rentals in Chesterfield

Guest favourite
Home in Wilmington
5 out of 5 average rating, 13 reviews

SKI Chalet-Pets-MtSnow-ChimneyHill-GameRm-IndrPool

LynnRating, 5 stars3 weeks ago
Shannon’s place was perfect for our Christmas visit with our son. Clean, spacious, great location, fully stocked, and made the perfect place to host our son and his Copper Mountain colleagues for Christmas!
Guest favourite
Apartment in Dover
5 out of 5 average rating, 13 reviews

Cozy condo with direct mountain views and shuttle

RomanRating, 5 stars4 weeks ago
Elizabeth is a phenomenal host, the place is one of the best I ever stayed in.. super clean, well stocked, (especially the kitchen made great impression) very clean.. An excellent value for the money… big and accommodating…
Guest favourite
Townhouse in Winhall
4.96 out of 5 average rating, 25 reviews

New! Vermont Getaway! Stratton - close to skiing!

KatherynRating, 5 stars4 weeks ago
Excellent location with great parking in a well maintained condo. We had seven people and everyone felt really comfortable. We were able to cook a meal easily and watch a movie after skiing with the family. The rooms are the perfect size and the views are so peaceful. Only a four min drive to Stratton, so it made our weekend simple.
Guest favourite
Home in Monroe
4.93 out of 5 average rating, 14 reviews

The Camp

BrendaRating, 5 stars1 month ago
We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!
Superhost
Home in Washington
4.73 out of 5 average rating, 15 reviews

Rustic Countryside Charm on 5 acres

PamRating, 5 stars1 month ago
this was a last minute booking and everything was great. April was very efficient and responsive. no problems at all while we were there. Had snowfall the night we arrived , had to shovel out, that would have been nice to have a plow to plow the driveway, but we got out ok, but that was it. Between the 4 adults, we got it done for the most part. It was a very nice stay, thank you April.
Superhost
Home in Manchester
4.86 out of 5 average rating, 35 reviews

Your VT Ski House: Fireplace, Indoor Pool, Dogs

AtulRating, 5 stars7 months ago
Beautiful area great amenity. Wish there was 1/2 bath downstairs. That was the only inconvenience.
Guest favourite
Home in Dover
4.89 out of 5 average rating, 70 reviews

Large Mount Snow Ski House with Hot Tub

AndyRating, 5 stars1 week ago
Big group of friends and I stayed at Michele's place for a ski-weekend at Mount Snow. House was comfortable and fun with lots of games in the basement and space for us to hang out as a group in the main living area. Hot tub was 🧑‍🍳 perfection. Michele was responsive and helpful via messages.
Guest favourite
Home in Wilmington
4.87 out of 5 average rating, 101 reviews

Close- > MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

AkhilRating, 5 stars1 month ago
The place was amazing. It was what the pictures show plus much more. Me and 10 of my friends slept comfortably and had a great time. Many games, nice kitchen, clean rooms and bathrooms, and if you’re a winter lover, hope it snows because this yard is amazing. We went sledding like kids again it was great. Definitely recommend. Right near mt. Snow and town of Wilmington which has great food options. Overall, quite the memorable stay.

Destinations to explore