Holiday rentals in Chesterfield

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Popular amenities for Chesterfield holiday rentals

Other great holiday rentals in Chesterfield

Guest favourite
Flat in Conway
4.96 out of 5 average rating, 25 reviews

Spacious, Sunny* Woodland Retreat

MollyRating, 5 stars4 days ago
We had a fantastic stay at Erica's with our 2 month old. Erica provided a crib, and it was safe for infant sleeping. We enjoyed sitting on the porch, and ended up cooking a full dinner for local friends one night. The kitchen had all the basics that we needed. It was a short trip so we didn't have much time to explore the property, but it looked beautiful and we enjoyed hearing the frogs at night and birds during the day. The apartment is HUGE, and we found it very comfortable. It'll be our go-to for future visits in the area!
Top guest favourite
Cabin in Becket
5 out of 5 average rating, 5 reviews

WALK to lake! Dog friendly, A-Frame in Berkshires!

AustinRating, 5 stars1 week ago
What more could you want? This quaint cabin situated in the woods offers privacy, unique architecture, comfort, and peace. It’s equipped with everything you could possibly need, and the hosts were truly some of the most responsive and kind people I have ever interacted with. They truly went above and beyond for us. We stayed with a toddler and two dogs, and they all loved the property and the cabin. We will most definitely be back!
Guest favourite
Home in Ashfield
4.98 out of 5 average rating, 57 reviews

An 18th century farmhouse

NateRating, 5 stars5 days ago
What a beautiful, idyllic getaway Susan offers for her guests. A kind welcoming soul who provides a stay that brings you back in history – we had the most lovely time!
Guest favourite
Cabin in Cambridge
4.97 out of 5 average rating, 31 reviews

Pond View Cabin. Off-Grid, Rustic & Dog Friendly.

EmilyRating, 5 stars1 week ago
Highly recommend Brian’s off grid cabin! His directions were very helpful and made navigating the generator, camp shower, and other on-site details super easy to understand and execute. His property is beautiful and peaceful. We’re already looking at our calendars for another time to visit. Our dog, Stumpy, very much enjoyed the outdoor access and pond. He didn’t want to leave!
Superhost
Cottage in Williamsburg
4.75 out of 5 average rating, 73 reviews

A Place for Peace - perfectly imperfect!

JenRating, 5 stars8 months ago
Comfortable with beautiful surroundings. Very responsive host.
Top guest favourite
Home in Chesterfield
4.98 out of 5 average rating, 58 reviews

High Field Farm

CatherineRating, 5 stars1 week ago
Such a relaxing place, space for everyone to spread out and to gather…kids played in the barn because it was a rainy weekend and sadly too cold for a swim. Great kitchen with all necessities. four minutes to gorge trail head where my son ran 50 miles in the beast coast ultra. highly recommend
Guest favourite
Home in Guilford
4.92 out of 5 average rating, 49 reviews

Vermont Mirror House

GeorgeRating, 5 stars5 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 Conway
4.99 out of 5 average rating, 95 reviews

House Above the Hollow

AnnaRating, 5 stars2 weeks ago
Meg’s place was truly amazing. The apartment itself was very well maintained, well-appointed, and Meg went out of her way to ask what kind of milk/creamer we liked with our coffee so that she had stocked in our fridge upon arrival. The property is stunning- from Meg’s flower beds to her gardens, to the open fields, to the bird feeds attracting the most beautiful birds, this property is truly serene and a place where we felt relaxed. Our visit was filled with hiking, biking, and exploring nearby towns (Northampton, Amherst, Hadley, etc.). Meg herself is an incredibly talented artist and has beautiful pottery she crafts in her studio located under the apartment. She was kind enough to show us the studio and sell us a couple of her beautiful vases which we know we’ll always think of our wonderful trip whenever we see them. Thanks for everything, Meg!

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