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May 1 - May 2
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May 2 - May 3
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May 3 - May 5
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May 10 - May 12

Compare 35 Cottages in Chesterfield with updated reviews, rates, and availability.

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.2 out of 10, Wonderful, (23)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Waterfront Cottage on Scenic Sportsman Pond
Exterior
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, (34)
"Linda was wonderful in her review of the property and was very accommodating in all aspects of our stay. The cottage was well equipped and very comfortable including the mattress. We enjoyed the lake and a little fishing. The area is very nice and we did some exploring. It was very quiet and we rarely even saw anyone while we were on the lake. We hope to return in the spring or summer. Many thanks to Linda and Brad"
Waterfront Cottage on Scenic Sportsman Pond
Cozy Cottage Along Idyllic Green River
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (32)
"Perfect litle getaway. Not to far from town, beautiful surrounding area, exactly what i was looking for."
Cozy Cottage Along Idyllic Green River
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Cottage on Laurel Lake, Private lake access, picture perfect sunsets
Interior
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
9.0 out of 10, Wonderful, (2)
"It is a fun place for kids with a beautiful lake to enjoy. We made many fun memories and enjoyed our stay very much."
Cottage on Laurel Lake, Private lake access, picture perfect sunsets
Charming Jaffrey Cottage w/ Deck & Grill!
Fridge, microwave, stovetop, dishwasher
Charming Jaffrey Cottage w/ Deck & Grill!
10.0 out of 10, Exceptional, (34)
"Loved everything about it!"
Charming Jaffrey Cottage w/ Deck & Grill!
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Exterior
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Historic Home w/ Modern Updates on 3.5 Acres
Interior
Historic Home w/ Modern Updates on 3.5 Acres
3.5 star property
10.0 out of 10, Exceptional, (1)
Historic Home w/ Modern Updates on 3.5 Acres
Cozy Falls Brook Cabin: Hike & Swim On-site!
Interior
Cozy Falls Brook Cabin: Hike & Swim On-site!
3.5 star property
Cozy Falls Brook Cabin: Hike & Swim On-site!
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Interior
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
3.5 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Interior
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.5 star property
10.0 out of 10, Exceptional, (1)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Jacksonville Cabin w/ Wraparound Deck & Views
Interior
Jacksonville Cabin w/ Wraparound Deck & Views
3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Interior
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
3.5 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Chic Wilmington Retreat w/ Deck: Walk to Downtown!
Interior
Chic Wilmington Retreat w/ Deck: Walk to Downtown!
3.0 star property
Chic Wilmington Retreat w/ Deck: Walk to Downtown!
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Interior
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Cozy 'green Mountain Chalet' in Putney Town
Interior
Cozy 'green Mountain Chalet' in Putney Town
3.0 star property
Cozy 'green Mountain Chalet' in Putney Town
Spacious Dover Home w/ Sauna < 5 Miles to Ski!
Interior
Spacious Dover Home w/ Sauna < 5 Miles to Ski!
3.0 star property
10.0 out of 10, Exceptional, (1)
"we enjoyed all of the space and the location a short distance from the resort. very comfortable stay for a group of five."
Spacious Dover Home w/ Sauna < 5 Miles to Ski!
Charming Jaffrey Cottage w/ Deck & Grill!
Interior
Charming Jaffrey Cottage w/ Deck & Grill!
3.5 star property
Charming Jaffrey Cottage w/ Deck & Grill!
Cozy Vermont Escape w/ Deck, Near Skiing!
Interior
Cozy Vermont Escape w/ Deck, Near Skiing!
3.0 star property
Cozy Vermont Escape w/ Deck, Near Skiing!
'john's Farmhouse in Mount Snow' on 120 Acres!
Interior
'john's Farmhouse in Mount Snow' on 120 Acres!
3.5 star property
'john's Farmhouse in Mount Snow' on 120 Acres!
Spacious Wilmington Home w/ Game Room & Deck!
Interior
Spacious Wilmington Home w/ Game Room & Deck!
3.5 star property
Spacious Wilmington Home w/ Game Room & Deck!
Don't see what you're looking for?
See all available properties in Chesterfield
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Chesterfield

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.2 out of 10, Wonderful, (23)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Charming Waterfront Log Cabin
Interior
Charming Waterfront Log Cabin
10.0 out of 10, Exceptional, (23)
"My husband and I stayed for 2 nights at this lovely log cabin on the pond. Although the weather did not cooperate outdoors, we had all the comforts of home indoors. The cabin was warm and toasty and the view out to the pond did not disappoint-fog rising on the water in the morning, steady rain throughout the day and then clearing at night with a moon reflected on the water. The cabin is stocked with games and the tv/streaming easy to navigate. If you want peace and quiet this is the cabin to...
Charming Waterfront Log Cabin
Beautiful, private log cabin with huge, relaxing screened porch
Property grounds
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (24)
"The house was very comfortable for our family. It was well-stocked with plates, pots, and pans. Bed were comfortable."
Beautiful, private log cabin with huge, relaxing screened porch
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chesterfield Cottages information

Number of reviews
109
Accommodation
35 Cottages
Lowest Price
Highest Price

Frequently asked questions

Why book your cottage in Chesterfield with Expedia?
Booking a cottage in Chesterfield is as easy as clicking on your travel dates and picking your ideal place for outdoor fun and relaxation. From luxurious retreats to inexpensive properties and cottages that feature perks like a pool, Expedia has something for all traveler styles. As for unbeatable deals? We’ve have them as well!
How can I find cheap cottages in Chesterfield?
The simplest way to locate cheap cottages in Chesterfield is with Expedia’s user-friendly filter tool. Narrow your search results by star rating, amenities and budget to grab unbeatable rates in a few clicks.
What is there to do in Chesterfield near my cottage?
Chesterfield has enough sights and activities to keep you occupied for weeks, beginning with Pisgah State Park. Actors Theatre Playhouse, Next Stage Arts and Spofford Lake are other well-known attractions. If you have more time, Stonewall Farm and Asbury United Methodist Church are nice final touches to your itinerary.

Recent reviews of Chesterfield hotels
Expedia verified reviews

The Covered Bridge Inn

The Covered Bridge Inn

5/5 Excellent
"This is a cheap hotel that is out of date but the room was spotless, no odors in room or bed! Very comfortable beds. Breakfast was basic but great bagels and real orange juice! The bat/shower looked brand new. Orbitz description said hotel was staffed until 11:00 pm but I called them to let them know we would be coming later and was told they are only there until 9:00 pm. They had a secure system for getting our key and it was easy snd flawless. Would def stay here again when needing a cheap clean room for the night. Also liked that Dunkin, Wendy’s and McDonalds are next door. "
A verified traveler stayed at The Covered Bridge Inn
Posted 1 day ago
The Covered Bridge Inn