A stone bridge over a river with a waterfall and a small building on the right.

Holiday Rentals in Town of Chesterfield

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Our top choices for Town of Chesterfield holiday rentals

A covered outdoor seating area with a ceiling fan, a cushioned sofa, and two armchairs.

1. High Peaks Haven is in the heart of Adirondack. Come enjoy with famil

High Peaks Haven is in the heart of Adirondack. Come enjoy with famil
Keeseville
8.0 out of 10, Very good, (6 reviews)
"House was perfect for the 4 of us . All the amenities we needed. Even had a bowl of assorted snacks waiting for us as well as coffee, kcups, etc . Would definitely book again."
United States
Frances l.
The price is €372
includes taxes & fees
13 Sept - 14 Sept
High Peaks Haven is in the heart of Adirondack. Come enjoy with famil
A gazebo with a wooden railing, surrounded by tables and chairs, and decorated with string lights.

2. The Wilderness Inn

The Wilderness Inn
3.0 star property
Wilmington
9.2 out of 10, Wonderful, (170 reviews)
"A calm place for a resting day and near to the high falls gorge and white face mountain attractions"
United States
Rajkumar
The price is €166
includes taxes & fees
17 Sept - 18 Sept
The Wilderness Inn
A modern kitchen with wooden accents, a dining area with a large table, and a bar area with stools.

3. Lake Placid Inn: Residences

Lake Placid Inn: Residences
3.0 star property
Lake Placid
9.0 out of 10, Wonderful, (330 reviews)
"A very nice place for the one night that we needed it."
United States
Donald
The price is €117
includes taxes & fees
13 Sept - 14 Sept
Lake Placid Inn: Residences
An outdoor patio area with wicker furniture, a glass table, and a decorative sailboat model.

4. Newly Updated Cozy Home ~ Located Downtown, UVM, Hospital Includes 8 Bikes!

Newly Updated Cozy Home ~ Located Downtown, UVM, Hospital Includes 8 Bikes!
South End
10.0 out of 10, Exceptional, (44 reviews)
"Perfect spot for visiting our student at UVM. Close to the school and church street and the owner had so many thoughtful extras. Worked out great for us. "
United States
Michelle G.
The price is €430
includes taxes & fees
13 Sept - 14 Sept
Newly Updated Cozy Home ~ Located Downtown, UVM, Hospital Includes 8 Bikes!
A covered patio with a wooden ceiling, a white wicker chair, a purple sofa, and a glass door leading to an indoor area.

5. 2 Mi to Main Street! Cozy Burlington Guest Suite

2 Mi to Main Street! Cozy Burlington Guest Suite
3.0 star property
New North End
10.0 out of 10, Exceptional, (1 review)
"I absolutely loved this rental! What a dream spot- cozy, privacy, the owner was so nice but also wasn’t intruding, the garden was beautiful it felt like walking into a fairy garden to get to the rental each day. It felt so safe which is an absolute must. And just made our trip delightful. Would absolutely rent here again!"
United States
Bethany
The price is €230
includes taxes & fees
8 Oct - 9 Oct
2 Mi to Main Street! Cozy Burlington Guest Suite
A wooden table with plates, glasses, and a bottle, set against a scenic lake view.

6. ZaLo House Waterline cabin with Hot Tub Pets

ZaLo House Waterline cabin with Hot Tub Pets
Peru
10.0 out of 10, Exceptional, (16 reviews)
"It was a beautiful place!"
United States
Caitlin W.
The price is €461
includes taxes & fees
20 Sept - 21 Sept
ZaLo House Waterline cabin with Hot Tub Pets
A room with a brown leather sofa, a wooden chair, and large windows with white frames.

7. 2 BR 3 Min Walk to Medical Center and UVM!

2 BR 3 Min Walk to Medical Center and UVM!
Centennial
9.4 out of 10, Exceptional, (92 reviews)
"Cindy was there to greet us with fresh eggs & cream for our breakfast and coffee!Cindy’s house was charming and comfortable. Will certainly stay there again!"
United States
maureen o.
The price is €373
includes taxes & fees
13 Sept - 14 Sept
2 BR 3 Min Walk to Medical Center and UVM!
A long wooden table with benches in a room with wooden floors and teal walls.

8. ADK Game House Rental

ADK Game House Rental
Au Sable Forks
9.6 out of 10, Exceptional, (19 reviews)
"Host was great, property was clean and as described. It was enjoyable and we highly recommend this VRBO"
United States
Andrew B.
The price is €927
includes taxes & fees
23 Sept - 24 Sept
ADK Game House Rental
A spacious kitchen with a central island, wooden cabinets, and a large window overlooking a deck.

9. High Peaks Hideaway - minutes from Whiteface Mt!

High Peaks Hideaway - minutes from Whiteface Mt!
Jay
10.0 out of 10, Exceptional, (6 reviews)
"Great property - would stay again"
United States
Carrie S.
The price is €479
includes taxes & fees
14 Sept - 15 Sept
High Peaks Hideaway - minutes from Whiteface Mt!
A cozy living room with a large sofa, a patterned rug, and a chandelier.

10. Downtown Designer Digs

Downtown Designer Digs
Downtown Burlington
9.8 out of 10, Exceptional, (33 reviews)
"Wonderful stay!"
United States
Carrie S.
The price is €289
includes taxes & fees
27 Sept - 28 Sept
Downtown Designer Digs
A kitchen with wooden cabinets, granite countertops, a built-in oven, and a stainless steel refrigerator.

11. 2BR house in a quiet neighborhood

2BR house in a quiet neighborhood
Plattsburgh
9.6 out of 10, Exceptional, (21 reviews)
"Everything was very clean, very conveniently located"
United States
Janmarie
The price is €295
includes taxes & fees
13 Sept - 14 Sept
2BR house in a quiet neighborhood
A two-story house with a balcony, a covered patio, and a well-maintained lawn.

12. Charming Studio Se7en apartment in tranquil Shelburne, perfect for your getaway!

Charming Studio Se7en apartment in tranquil Shelburne, perfect for your getaway!
Shelburne
10.0 out of 10, Exceptional, (13 reviews)
"Very nice studio with lovely yard and updated kitchen, bath and furniture. Well equipped kitchen with blender and loved the fresh cream and maple syrup."
United States
John & Sue T.
The price is €246
includes taxes & fees
14 Sept - 15 Sept
Charming Studio Se7en apartment in tranquil Shelburne, perfect for your getaway!
A house with a front porch, a door with a window, and a grassy yard with trees.

13. Comfy, sunny, Wi-fi + coffee Walk to Downtown Winooski

Comfy, sunny, Wi-fi + coffee Walk to Downtown Winooski
Winooski
9.6 out of 10, Exceptional, (24 reviews)
"Really nice place and great location. Definitely recommend."
United States
Michael A.
The price is €189
includes taxes & fees
13 Sept - 14 Sept
Comfy, sunny, Wi-fi + coffee Walk to Downtown Winooski
A modern kitchen with white cabinets, a built-in microwave, and a refrigerator.

14. Large cozy and peaceful apartment walk anywhere

Large cozy and peaceful apartment walk anywhere
Winooski
9.8 out of 10, Exceptional, (49 reviews)
"Great location, plenty of space and clean! "
United States
Justin E.
The price is €444
includes taxes & fees
13 Sept - 14 Sept
Large cozy and peaceful apartment walk anywhere
A modern living room with a black sofa, a coffee table, and a TV mounted on the wall.

15. Cozy- 2-Bedroom clean and Quiet- Maple St. Walk anywhere

Cozy- 2-Bedroom clean and Quiet- Maple St. Walk anywhere
South End
9.6 out of 10, Exceptional, (177 reviews)
"Clean, comfortable, and convenient parking. Would definitely stay again!"
United States
Kegan
The price is €261
includes taxes & fees
14 Sept - 15 Sept
Cozy- 2-Bedroom clean and Quiet- Maple St. Walk anywhere
A wooden cabin with a sliding glass door leading to an outdoor deck. Inside, there is a wooden table and two rocking chairs.

16. Adirondack Riverfront Retreat

Adirondack Riverfront Retreat
Jay
10.0 out of 10, Exceptional, (81 reviews)
"This was such a fun and cozy weekend getaway! Very clean and quiet."
United States
Jessica K.
The price is €335
includes taxes & fees
13 Sept - 14 Sept
Adirondack Riverfront Retreat
A two-story house with a balcony, a patio with outdoor furniture, and a large window.

17. Swim, Boat & Explore! Lake Champlain Retreat!

Swim, Boat & Explore! Lake Champlain Retreat!
3.0 star property
Malletts Bay
The price is €1,068
includes taxes & fees
30 Sept - 1 Oct
Swim, Boat & Explore! Lake Champlain Retreat!
A kitchen with a white stove, stainless steel pots, a brass faucet, and various kitchen items on the counter.

18. New 2024 Cottage Near Beaches & Bike Path

New 2024 Cottage Near Beaches & Bike Path
New North End
10.0 out of 10, Exceptional, (4 reviews)
"This place is amazing! Very clean and well stocked, even coffee. All the little touches make it such a wonderful place to stay. There is ample room for 4 people to sleep comfortably. Highly recommended."
United States
Debra C.
The price is €277
includes taxes & fees
22 Sept - 23 Sept
New 2024 Cottage Near Beaches & Bike Path
A covered porch with brick walls, a white railing, and a colorful geometric-patterned floor.

19. Historic Charm Meets Modern Comfort in Downtown Burlington

Historic Charm Meets Modern Comfort in Downtown Burlington
Burlington
10.0 out of 10, Exceptional, (69 reviews)
"Excellent location and space. We thoroughly enjoyed our stay and will rebook."
United States
Marc E.
The price is €234
includes taxes & fees
13 Sept - 14 Sept
Historic Charm Meets Modern Comfort in Downtown Burlington
A dining room with a wooden table, six chairs, a chandelier, and a rug.

20. Charming 4BR House - Burlington

Charming 4BR House - Burlington
Old North End
9.6 out of 10, Exceptional, (26 reviews)
"Very clean and close to everything. "
United States
Michelle V.
Charming 4BR House - Burlington
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.
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Top Town of Chesterfield Hotel Reviews

Vermont Suites

Vermont Suites

10/10 Excellent
"Such a cute, clean and comfortable stay. Not far from down town Burlington, Vt."
Grainger 1-night trip
Posted 3 hours ago
Vermont Suites

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Holiday Homes in Town of Chesterfield

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