Holiday Rentals in Town of Chesterfield

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Our top choices for Town of Chesterfield holiday rentals

Property grounds
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

High Peaks Haven is in the heart of Adirondack. Come enjoy with famil
Keeseville
8.0 out of 10, Very good, (6)
"Check in was convenient and easy.Amir was very helpful.Kitchen facilities are complete and accessible.Great job. Neat and tidy house!"
United States
richard a.
The price is €397
includes taxes & fees
4 Jan - 5 Jan 2026
High Peaks Haven is in the heart of Adirondack. Come enjoy with famil
Gazebo
The Wilderness Inn

The Wilderness Inn

The Wilderness Inn
3.0 star property
Wilmington
9.2 out of 10, Wonderful, (165)
"Our family had an amazing stay. The place was spotless and cozy. The kitchen had everything we needed and more. The cabin was warm and the fireplace gave it a nice rustic touch. "
United States
Gabriella
The Wilderness Inn
Premium bedding, down duvets, pillow-top beds, desk
Lake Placid Inn: Residences

Lake Placid Inn: Residences

Lake Placid Inn: Residences
3.0 star property
Lake Placid
8.8 out of 10, Excellent, (285)
"Perfect location easy access to everything needed including town, grocery and mountains. "
United States
Roger
The price is €115
includes taxes & fees
12 Jan - 13 Jan 2026
Lake Placid Inn: Residences
Exterior
Lake Placid Inn Main Street

Lake Placid Inn Main Street

Lake Placid Inn Main Street
2.0 star property
Lake Placid
9.2 out of 10, Wonderful, (164)
"Staff was very nice and the room was very clean and comfortable."
United States
Barbara
The price is €106
includes taxes & fees
19 Jan - 20 Jan 2026
Lake Placid Inn Main Street
Fridge, microwave, oven, stovetop
1bdrm Apt near UVMMC, i89, and Downtown

1bdrm Apt near UVMMC, i89, and Downtown

1bdrm Apt near UVMMC, i89, and Downtown
Winooski
9.8 out of 10, Exceptional, (6)
"The place was as advertised and very cozy and pleasant."
United States
Melissa M.
The price is €209
includes taxes & fees
28 Dec - 29 Dec
1bdrm Apt near UVMMC, i89, and Downtown
Superior Apartment, Pets allowed, Mountain View | Living area
Central Lake Placid Mountain Views

Central Lake Placid Mountain Views

Central Lake Placid Mountain Views
3.5 star property
Lake Placid
The price is €743
includes taxes & fees
9 Jan - 10 Jan 2026
Central Lake Placid Mountain Views
Exterior
Apartment in historic farmhouse

Apartment in historic farmhouse

Apartment in historic farmhouse
Milton
9.6 out of 10, Exceptional, (125)
"Great location. Very nice hosts. "
United States
Margaret D.
The price is €162
includes taxes & fees
6 Jan - 7 Jan 2026
Apartment in historic farmhouse
Exterior detail
Cozy Studio 1/2 block to Church St & Shops-Pets

Cozy Studio 1/2 block to Church St & Shops-Pets

Cozy Studio 1/2 block to Church St & Shops-Pets
Old North End
9.6 out of 10, Exceptional, (12)
"Great location (central to great restaurants, venues, etc) and provided everything we needed including parking."
United States
Alicia B.
The price is €136
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy Studio 1/2 block to Church St & Shops-Pets
Property grounds
Luxury Lakefront 4BR w/ Beach

Luxury Lakefront 4BR w/ Beach

Luxury Lakefront 4BR w/ Beach
2.0 star property
Colchester
10.0 out of 10, Exceptional, (7)
"This place is great. Located right on the lake. Everything in house is brand new. Very clean and comfortable. Stay here if you're in the area"
United States
stephen s.
The price is €1,506
includes taxes & fees
20 Jan - 21 Jan 2026
Luxury Lakefront 4BR w/ Beach
Private kitchen
Little downtown gem with parking

Little downtown gem with parking

Little downtown gem with parking
2.0 star property
Old North End
9.8 out of 10, Exceptional, (22)
"Very clean and comfortable, would stay here again."
United States
Greta F.
The price is €153
includes taxes & fees
29 Dec - 30 Dec
Little downtown gem with parking
Exterior
Charming 2-bedroom house in welcoming Winooski with WiFi, laundry Pets&fence

Charming 2-bedroom house in welcoming Winooski with WiFi, laundry Pets&fence

Charming 2-bedroom house in welcoming Winooski with WiFi, laundry Pets&fence
2.0 star property
Winooski
10.0 out of 10, Exceptional, (26)
"This house was perfect!"
United States
Kimberly K.
The price is €205
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 2-bedroom house in welcoming Winooski with WiFi, laundry Pets&fence
Exterior
Cozy Private Suite - Near BTV Airport & UVM

Cozy Private Suite - Near BTV Airport & UVM

Cozy Private Suite - Near BTV Airport & UVM
2.0 star property
South Burlington
9.0 out of 10, Wonderful, (8)
"It was cute and located in a great neighborhood."
United States
Sara G.
The price is €177
includes taxes & fees
19 Jan - 20 Jan 2026
Cozy Private Suite - Near BTV Airport & UVM
Microwave, oven, stovetop
Perfect Burlington Stay – Cozy 1BR w/ Balcony, 5 min Walk to Church St & Lake

Perfect Burlington Stay – Cozy 1BR w/ Balcony, 5 min Walk to Church St & Lake

Perfect Burlington Stay – Cozy 1BR w/ Balcony, 5 min Walk to Church St & Lake
Old North End
9.6 out of 10, Exceptional, (5)
"It was the BEST home I've ever been to!!If anyone sees this review, I highly recommend that you reserve this place right away!"
Canada
YoonJae L.
The price is €231
includes taxes & fees
20 Jan - 21 Jan 2026
Perfect Burlington Stay – Cozy 1BR w/ Balcony, 5 min Walk to Church St & Lake
1 bedroom, WiFi
Double Queen Room - 2QD

Double Queen Room - 2QD

Double Queen Room - 2QD
Lake Placid
9.6 out of 10, Exceptional, (5)
"We had a fantastic experience staying here! The room was recently renovated, clean, well-appointed, and very comfortable. Everything—from the linens to the bathroom—felt fresh and well cared for.The location is unbeatable—just a short walk to Main Street, where you’ll find great restaurants, shops, and beautiful views of Mirror Lake. It was so convenient to explore the town without needing to drive or worry about parking.The host was friendly and responsive, and check-in was smooth and easy. I’d...
Canada
Sergio A.
The price is €116
includes taxes & fees
29 Dec - 30 Dec
Double Queen Room - 2QD
Private kitchen
ADK cottage with Mountain Views

ADK cottage with Mountain Views

ADK cottage with Mountain Views
2.0 star property
Saranac
8.8 out of 10, Excellent, (6)
"Great property, great views, great communication. Easy process, thanks! "
United States
Alexandria M.
The price is €275
includes taxes & fees
4 Jan - 5 Jan 2026
ADK cottage with Mountain Views
Fridge, microwave, oven, stovetop
Charming 2-bedroom cabin in the Adirondacks with a treehouse and an artist loft

Charming 2-bedroom cabin in the Adirondacks with a treehouse and an artist loft

Charming 2-bedroom cabin in the Adirondacks with a treehouse and an artist loft
2.0 star property
Elizabethtown
10.0 out of 10, Exceptional, (3)
"The place was perfect!"
United States
Deb J.
The price is €406
includes taxes & fees
7 Jan - 8 Jan 2026
Charming 2-bedroom cabin in the Adirondacks with a treehouse and an artist loft
TV
Cozy- 2-Bedroom clean and Quiet- Maple St. Walk anywhere

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, (156)
"Great location central to everything"
United States
Joanne R.
The price is €185
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy- 2-Bedroom clean and Quiet- Maple St. Walk anywhere
Property grounds
Comfy, sunny, Wi-fi + coffee Walk to Downtown Winooski

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

Comfy, sunny, Wi-fi + coffee Walk to Downtown Winooski
2.0 star property
Winooski
9.8 out of 10, Exceptional, (12)
"Great place, would stay again! "
United States
christine b.
The price is €187
includes taxes & fees
30 Dec - 31 Dec
Comfy, sunny, Wi-fi + coffee Walk to Downtown Winooski
Exterior detail
Historic Charm Meets Modern Comfort in Downtown Burlington

Historic Charm Meets Modern Comfort in Downtown Burlington

Historic Charm Meets Modern Comfort in Downtown Burlington
Burlington
10.0 out of 10, Exceptional, (49)
"Great place. Good location. Highly recommend. "
United States
Cory G.
The price is €181
includes taxes & fees
7 Jan - 8 Jan 2026
Historic Charm Meets Modern Comfort in Downtown Burlington
Economy Apartment, City View
Cozy Modern Home

Cozy Modern Home

Cozy Modern Home
3.5 star property
Lake Placid
The price is €773
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Modern Home
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
"Clean room, great amenities, excellent restaurants, and cute, friendly goats."
Helen 4-night trip
Posted 2 days ago
The Essex Resort & Spa

Find out more about Town of Chesterfield

Holiday Homes in Town of Chesterfield

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