
Holiday rentals in Chesterfield
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Top-rated holiday rentals in Chesterfield
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Other great holiday rentals in Chesterfield
Guest favourite

Cabin in Dummerston
5 out of 5 average rating, 13 reviewsPeaceful A-Frame in VT | Sauna, River, Cozy Porch
JakeRating, 5 stars2 weeks ago
Great place to stay if you’re looking for a peaceful retreat into the woods. This is a quaint, quiet retreat that provided us a relaxing getaway from the city. The property is surrounded by lush greenery and a beautiful stream. Inside, the projector makes for awesome movie nights. The kitchen provided everything one would need. The bedroom is good, but be mindful of a large step up to get into bed. This place isn’t for the faint of heart if bugs aren’t your thing. Came across a bit, but friendly spider and our dog picked up a couple of ticks. Nothing the hosts can do and they provided tick spray. The hosts are super responsive, helpful, and accommodating. You can’t ask for a better host honestly. Great place, highly recommend!
Superhost

Cabin in Dummerston
4.87 out of 5 average rating, 45 reviewsCoverd Bridge Cabin
JelaniRating, 5 stars2 weeks ago
This was everything we asked for and more! Beautiful cabin with amazing views, privacy and amenities inside and out. A lovely hiking trail with access right in your backyard, a stream as well and plenty of seating. Everything you would need and imagine for a weekend getaway just to enjoy the peace and tranquility to connect with nature is right here. Couldn’t ask for a better experience.
Guest favourite

Flat in Putney
4.97 out of 5 average rating, 97 reviewsMinimal organic hideaway inspired by nature
ItaRating, 5 stars2 weeks ago
Katherine’s space was so cozy! It was exactly what I needed for a retreat from daily life. I found both the loft and the daybed very comfortable. There were dimmers on most of the light fixtures, which was important to me because I like low-light settings. The kitchen included a counter with stools and was really quite beautiful. This Airbnb was within walking distance to a local restaurant, the general store and a food co-op. I decided not to rent a car because I was there for R&R., however , if you had a car, just a few minutes outside of town you would see beautiful trees all with leaves in there spring splendor. You could get to Brattleboro in about 20 minutes if you’re looking for more choices of restaurants.. (I decided to take the train up so I took a taxi to the Airbnb from the train and back to the train at the end of my trip.). Although it rained most of the time I was there, it was perfect for my goal of R&R.
Guest favourite

Cabin in Brookline
4.94 out of 5 average rating, 17 reviewsOff-the-Grid Cabin in the Forest
AndrewRating, 5 stars2 weeks ago
Ideal cabin in the woods for a secluded forest getaway - well stocked kitchen, and the outhouse is 10/10. Very responsive and helpful!
Top guest favourite

Place to stay in Chesterfield
5 out of 5 average rating, 49 reviewsThe Ultimate Romantic Getaway
StephanieRating, 5 stars8 months ago
The hosts were so friendly and the place is truly beautiful. The “glamping” tent was spacious, super comfortable, and had all the amenities. It allowed us to enjoy the beauty & peace of the outdoors with all of the typical comforts of being indoors. The surrounding wood pergolas / porch / patios each had their own unique features to enjoy during different parts of the day! Wonderful and romantic getaway!
Guest favourite

Cabin in Brattleboro
4.94 out of 5 average rating, 17 reviewsHidden Forest Cabin: Kitchen, Deck, Babbling Brook
AmyRating, 5 stars2 weeks ago
The house is wonderful - beautiful setting, clean and comfy. Everything you need to enjoy a get away. A short drive to Brattleboro which has plenty of restaurants and stores to enjoy. Theresa and Megan were great hosts. They were very responsive and provided easy to follow instructions plus recommendations of places to eat and explore. Our highlight was breakfast on the deck looking out onto the brook. A very peaceful and beautiful setting. We hope to return.
Guest favourite

Home in Guilford
4.94 out of 5 average rating, 48 reviewsVermont Mirror House
GeorgeRating, 5 stars4 days ago
I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.
Top guest favourite

Flat in Brattleboro
4.97 out of 5 average rating, 76 reviewsBright and Modern Chestnut Street Apartment
MatthewRating, 5 stars5 days ago
We had a wonderful time staying at Lucia's home. It was spotless, had everything we needed, and was beautifully decorated. We can't recommend this stay enough! Thanks again, Lucia!
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- Stratton Mountain
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