A mountainous landscape with autumn foliage, a winding road, and a clear sky.

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 €389
includes taxes & fees
28 Oct - 29 Oct
High Peaks Haven is in the heart of Adirondack. Come enjoy with famil
A modern kitchen with wooden accents, a dining area with a large table, and a bar area with stools.

2. Lake Placid Inn: Residences

Lake Placid Inn: Residences
3.0 star property
Lake Placid
9.0 out of 10, Wonderful, (345 reviews)
"Had a very nice stay"
United States
David
The price is €121
includes taxes & fees
1 Nov - 2 Nov
Lake Placid Inn: Residences
A cabin with a porch and outdoor seating area surrounded by tall trees.

3. The Wilderness Inn

The Wilderness Inn
3.0 star property
Wilmington
9.2 out of 10, Wonderful, (171 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 €108
includes taxes & fees
28 Oct - 29 Oct
The Wilderness Inn
A modern kitchen with white cabinets, a stainless steel refrigerator, a dishwasher, a stove, and a microwave.

4. Little downtown gem with parking

Little downtown gem with parking
Old North End
9.6 out of 10, Exceptional, (42 reviews)
"Great location and cozy."
United States
Ken L.
The price is €202
includes taxes & fees
24 Nov - 25 Nov
Little downtown gem with parking
A modern living room with a dining area, large windows, and a balcony with a view.

5. Lake Placid Inn Main Street

Lake Placid Inn Main Street
2.0 star property
Lake Placid
9.0 out of 10, Wonderful, (199 reviews)
"Very clean room and nice staff!"
United States
Kate
The price is €121
includes taxes & fees
1 Nov - 2 Nov
Lake Placid Inn Main Street
A living room with a sofa, coffee table, and a TV. There is a kitchen visible in the background with wooden cabinets and a TV.

6. 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, (185 reviews)
"Clean, comfortable, and convenient parking. Would definitely stay again!"
United States
Kegan
The price is €223
includes taxes & fees
12 Nov - 13 Nov
Cozy- 2-Bedroom clean and Quiet- Maple St. Walk anywhere
A two-story house with a balcony, a patio with outdoor furniture, and a large window.

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

Swim, Boat & Explore! Lake Champlain Retreat!
3.0 star property
Malletts Bay
The price is €601
includes taxes & fees
31 Oct - 1 Nov
Swim, Boat & Explore! Lake Champlain Retreat!
A room with a brown leather sofa, a wooden chair, and large windows with white frames.

8. 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, (97 reviews)
"Lovely 2BR ground floor apartment, plenty of space for 2 couples. Kitchen very adequately supplied with Kuerig as well as drip coffee maker and a hot water heater. Very accommodating host - she even moved her car to street parking so we had room for two cars. Excellent location."
United States
Susan
The price is €419
includes taxes & fees
27 Nov - 28 Nov
2 BR 3 Min Walk to Medical Center and UVM!
A compact room with a kitchenette, a bed, a desk with a lamp, and a ceiling light fixture.

9. City Nest.

City Nest.
Old North End
9.6 out of 10, Exceptional, (13 reviews)
"Location excellent, was in walking distance to church st marketplace, restaurants, coffee shops, bars etc. Appreciated having a dedicated parking spot & apartment was easy to access. Very petite but efficient room, had everything we needed and was very quiet at night."
United States
Alexandra
The price is €161
includes taxes & fees
28 Oct - 29 Oct
City Nest.
A wooden deck with a view of a forest and a cloudy sky.

10. Onion City Retreat: a place to relax and rejuvenate.

Onion City Retreat: a place to relax and rejuvenate.
Winooski
9.8 out of 10, Exceptional, (45 reviews)
"Great location and well appointed setup"
United States
Alan
The price is €169
includes taxes & fees
3 Nov - 4 Nov
Onion City Retreat: a place to relax and rejuvenate.
A house with a front porch, a door with a window, and a grassy yard with trees.

11. 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, (26 reviews)
"Really nice place and great location. Definitely recommend."
United States
Michael A.
The price is €198
includes taxes & fees
28 Oct - 29 Oct
Comfy, sunny, Wi-fi + coffee Walk to Downtown Winooski
A cozy living room with a blue sofa, a coffee table, and a dining area with a table and chairs.

12. Apartment in historic farmhouse

Apartment in historic farmhouse
Milton
9.6 out of 10, Exceptional, (142 reviews)
"Great location, very quiet and the goats were fun !!"
United States
Ellen O.
The price is €211
includes taxes & fees
8 Nov - 9 Nov
Apartment in historic farmhouse
A modern kitchen with white cabinetry, a granite countertop, stainless steel appliances, and a window providing natural light.

13. Lovely 2-Bedroom Condo, Close to Burlington/Airport!

Lovely 2-Bedroom Condo, Close to Burlington/Airport!
South Burlington
9.8 out of 10, Exceptional, (19 reviews)
"Great little unit in a convenient location near the airport and highway! We spent time in Burlington and Stowe and felt right at home. "
United States
Patrick G.
The price is €296
includes taxes & fees
3 Nov - 4 Nov
Lovely 2-Bedroom Condo, Close to Burlington/Airport!
A two-story house with a balcony, a covered patio, and a well-maintained lawn.

14. 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, (21 reviews)
"Cute place, very clean we had all the comforts of home."
United States
Ellen
Charming Studio Se7en apartment in tranquil Shelburne, perfect for your getaway!
A modern living room with a brown sofa, a patterned rug, a ceiling fan, and a kitchen in the background.

15. NEW!! Cozy Guest House with WiFi, Coffee Bar & Sunsets

NEW!! Cozy Guest House with WiFi, Coffee Bar & Sunsets
South Hero
9.8 out of 10, Exceptional, (47 reviews)
"We had a wonderful stay at the guest cottage. It was incredibly clean and a great location in South Hero. We would absolutely come back again! Thank you for a great stay!"
United States
Ali Z.
The price is €265
includes taxes & fees
29 Oct - 30 Oct
NEW!! Cozy Guest House with WiFi, Coffee Bar & Sunsets
A modern kitchen with stainless steel appliances, white cabinets, and a patterned backsplash.

16. City Chic 1BR Escape - Winooski

City Chic 1BR Escape - Winooski
Winooski
9.6 out of 10, Exceptional, (5 reviews)
"Cozy and nice place with everything we needed for graduation weekend. Convenient location."
United States
MICHAEL
The price is €176
includes taxes & fees
3 Nov - 4 Nov
City Chic 1BR Escape - Winooski
A modern, well-lit room with a brown leather sofa, a wooden coffee table, and a small armchair. There is a bed with a patterned bedspread in the background, a dresser with a mirror, and a painting on the wall.

17. Sweet & Cozy Studio Apartment

Sweet & Cozy Studio Apartment
South Burlington
10.0 out of 10, Exceptional, (6 reviews)
"It was nice and quiet"
United States
Jeffrey
The price is €209
includes taxes & fees
16 Nov - 17 Nov
Sweet & Cozy Studio Apartment
A living room with a gray sofa, a wooden cabinet, a small table with a blender, a colorful rug, and a door with a floral wallpaper.

18. Central Location, Cozy Studio with WiFi and AC in enchanting South Burlington

Central Location, Cozy Studio with WiFi and AC in enchanting South Burlington
South Burlington
9.8 out of 10, Exceptional, (14 reviews)
"Stayed for two nights, had a wonderful time! "
United States
JFimmers
Central Location, Cozy Studio with WiFi and AC in enchanting South Burlington
A bedroom with a bed, bedside table, lamp, and a small potted plant.

19. New Modern Studio- Hop Skip & Jump to Waterfront

New Modern Studio- Hop Skip & Jump to Waterfront
Downtown Burlington
9.6 out of 10, Exceptional, (31 reviews)
"A great stay for those that love all things walkable. Right by Lake Champlain, it's easy to find, convenient parking and easy to check in and out of. An amazing find!"
United States
paula
The price is €213
includes taxes & fees
28 Oct - 29 Oct
New Modern Studio- Hop Skip & Jump to Waterfront
A compact living space with a kitchenette, a sofa, a coffee machine, and a TV.

20. Cozy Private Suite - Near BTV Airport & UVM

Cozy Private Suite - Near BTV Airport & UVM
South Burlington
9.4 out of 10, Exceptional, (11 reviews)
"Very lovely space in a quiet neighborhood. Very conveniently located and walkable to many local restaurants, grocery stores, and other amenities. Highly recommended."
United States
Steven
Cozy Private Suite - Near BTV Airport & UVM
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

The Essex Resort & Spa

The Essex Resort & Spa

10/10 Excellent
"The spa facilities were excellent. Firepit was a nice touch as was the gas fire in the room. Would definitely stay again."
Stephen 3-night trip
Posted 1 hour ago
The Essex Resort & Spa

Find out more about Town of Chesterfield

Holiday Homes in Town of Chesterfield

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