
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 stars3 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!
Guest favourite

Home in Chesterfield
5 out of 5 average rating, 13 reviewsPicturesque Lakefront Retreat at Spofford Lake
AnaRating, 5 stars3 weeks ago
This was our second stay at Palmer’s place and we already can’t wait to go back. It always exceeds expectations. Palmer pays close attention to detail, making sure everything you need is within reach. The home itself is absolutely beautiful, matched only by the view of the lake from the main living area. Although it wasn’t quite warm enough for us to enjoy the outside activities, we thoroughly enjoyed relaxing inside, which speaks to how much the home has to offer. If you’re looking for a place to stay, look no further. This is truly a gem.
Guest favourite

Flat in Putney
4.97 out of 5 average rating, 97 reviewsMinimal organic hideaway inspired by nature
ItaRating, 5 stars3 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 Winchester
4.85 out of 5 average rating, 27 reviewsThe Ironclad Mountain Retreat
JenniferRating, 5 stars3 weeks ago
Could not have asked for a more perfect and peaceful stay at the mountain house. It is a dream of a place, in beautiful surroundings.
Guest favourite

Cabin in Brookline
4.94 out of 5 average rating, 17 reviewsOff-the-Grid Cabin in the Forest
AndrewRating, 5 stars3 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!
Guest favourite

Home in Guilford
4.92 out of 5 average rating, 49 reviewsVermont Mirror House
GeorgeRating, 5 stars1 week 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.
Guest favourite

Tiny home in Townshend
4.98 out of 5 average rating, 64 reviewsCheerful cabin retreat in the woods and mountains
NathanRating, 5 stars1 month ago
What an incredible place. Quiet, beautiful, restorative. The cabin's amenities make it easy to enjoy your time inside and outside the cabin. The bed and pillows are well-maintained and comfortable, and the sheets are of high quality. The light pollution is much lower here, so star gazing is an incredible experience. There are hiking/snowmobiling trails accessible by a short walk from the house. If it is tick season, be prepared with repellent!
Guest favourite

Guest suite in Putney
4.96 out of 5 average rating, 69 reviewsPeaceful Country Retreat on 15 Secluded Acres
MelanieRating, 5 stars3 days ago
We loved our stay ! It was located in a semi secluded location that is surrounded by woods . So waking up to the sound of rain or just nature is what you are going to get . 10 minutes from Putney Downtown area and about 20 minutes from Brattleboro . If you want peaceful sleep and even if you just want to get away to a serene spot . This is great !
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