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

Vacation Rentals in Town of Chesterfield

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Top Cities in Town of Chesterfield

A river flowing through a town with a red mill and houses in the background.
Vacation RentalsVacation Rentals

Keeseville

Keeseville

Our top choices for Town of Chesterfield vacation 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.
$404 nightly
The price is $456
Oct 18 - Oct 19
Total with taxes and fees
High Peaks Haven is in the heart of Adirondack. Come enjoy with famil
A cozy living room with a blue sofa, a coffee table, and a dining area with a table and chairs.

2. Apartment in historic farmhouse

Apartment in historic farmhouse
Milton
9.6 out of 10, Exceptional, (141 reviews)
"Cozy retreat on a beautiful river. Chad is very engaging. Friendly, knowledgeable and helpful. Will definitely stay again next time!!"
United States
David D.
$197 nightly
The price is $221
Oct 20 - Oct 21
Total with taxes and fees
Apartment in historic farmhouse
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, (341 reviews)
"Will definitely stay here again. Room so clean and the location was conveniently located to shops and a quick ride into town."
United States
Melissa
$129 nightly
The price is $135
Oct 18 - Oct 19
Total with taxes and fees
Lake Placid Inn: Residences
A gazebo with a wooden railing, surrounded by tables and chairs, and decorated with string lights.

4. 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
$154 nightly
The price is $174
Oct 18 - Oct 19
Total with taxes and fees
The Wilderness Inn
A modern kitchen with white cabinets, a stainless steel refrigerator, a dishwasher, a stove, and a microwave.

5. Little downtown gem with parking

Little downtown gem with parking
Old North End
9.6 out of 10, Exceptional, (40 reviews)
"Great location and cozy."
United States
Ken L.
$160 nightly
The price is $179
Oct 27 - Oct 28
Total with taxes and fees
Little downtown gem with parking
A compact living space with a kitchenette, a sofa, a coffee machine, and a TV.

6. 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
$210 nightly
The price is $238
Nov 4 - Nov 5
Total with taxes and fees
Cozy Private Suite - Near BTV Airport & UVM
A bedroom with a bed, a washing machine, and a small cabinet.

7. 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
$188 nightly
The price is $191
Nov 9 - Nov 10
Total with taxes and fees
City Chic 1BR Escape - Winooski
A compact room with a kitchenette, a bed, a desk with a lamp, and a ceiling light fixture.

8. City Nest.

City Nest.
Old North End
9.6 out of 10, Exceptional, (12 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
$169 nightly
The price is $190
Oct 28 - Oct 29
Total with taxes and fees
City Nest.
A kitchen with a granite countertop, stainless steel sink, and a toaster oven.

9. 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, (13 reviews)
"Stayed for two nights, had a wonderful time! "
United States
JFimmers
$159 nightly
The price is $180
Oct 27 - Oct 28
Total with taxes and fees
Central Location, Cozy Studio with WiFi and AC in enchanting South Burlington
A kitchen with a microwave, stove, and sink.

10. Convenient 1BR Close to Downtown

Convenient 1BR Close to Downtown
Winooski
9.2 out of 10, Wonderful, (23 reviews)
"Great location and very nice place! Easily walkable to restaurants and bars in Winooski or a quick drive/Uber to Church Street in Burlington. Would definitely stay again!"
United States
Mike B.
$201 nightly
The price is $204
Nov 4 - Nov 5
Total with taxes and fees
Convenient 1BR Close to Downtown
A modern kitchen with grey cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

11. Cozy 1BR in Winooski!

Cozy 1BR in Winooski!
Winooski
9.0 out of 10, Wonderful, (7 reviews)
$187 nightly
The price is $190
Nov 16 - Nov 17
Total with taxes and fees
Cozy 1BR in Winooski!
A compact living space with a kitchenette, a bed with patterned bedding, a small dining table, and a mounted TV.

12. Private Apt w/ parking spot shrt walk to Dwntwn!

Private Apt w/ parking spot shrt walk to Dwntwn!
Old North End
9.8 out of 10, Exceptional, (20 reviews)
"Lovely hosts and wonderful apartment! We stayed for 4 nights and we were so comfortable. Great location to everything in Burlington and beyond!"
United States
Sandy M.
$232 nightly
The price is $250
Oct 22 - Oct 23
Total with taxes and fees
Private Apt w/ parking spot shrt walk to Dwntwn!
A bedroom with a bed, a sofa, a small table, and a window.

13. Stylish Studio in the Queen City

Stylish Studio in the Queen City
Old North End
9.0 out of 10, Wonderful, (18 reviews)
"We really liked the location for our needs."
United States
Anna
$165 nightly
The price is $184
Oct 25 - Oct 26
Total with taxes and fees
Stylish Studio in the Queen City
A bedroom with a bed, bedside table, lamp, and a small potted plant.

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

New Modern Studio- Hop Skip & Jump to Waterfront
Downtown Burlington
9.6 out of 10, Exceptional, (28 reviews)
"Great apartment with all the amenities needed for a solo stay. Bed was firm (as I like it), great AC for warm summer days, and full sized washer and dryer. Location is unbeatable if you’re keen to be near the water front and the greenway path."
United States
Tray S.
$207 nightly
The price is $231
Oct 28 - Oct 29
Total with taxes and fees
New Modern Studio- Hop Skip & Jump to Waterfront
Private kitchen

15. The North End Pad

The North End Pad
Old North End
9.4 out of 10, Exceptional, (28 reviews)
"Good parking and lovation"
United States
Christopher
$165 nightly
The price is $184
Oct 27 - Oct 28
Total with taxes and fees
The North End Pad
A house with a front porch, a door with a window, and a grassy yard with trees.

16. 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, (25 reviews)
"Really nice place and great location. Definitely recommend."
United States
Michael A.
$190 nightly
The price is $215
Oct 25 - Oct 26
Total with taxes and fees
Comfy, sunny, Wi-fi + coffee Walk to Downtown Winooski
A wooden deck with a view of a forest and a cloudy sky.

17. 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
$162 nightly
The price is $183
Oct 25 - Oct 26
Total with taxes and fees
Onion City Retreat: a place to relax and rejuvenate.
A sidewalk cafe with outdoor seating and umbrellas.

18. Deluxe Cute Apt | 1min Walk Restaurants + Shops

Deluxe Cute Apt | 1min Walk Restaurants + Shops
Winooski
9.4 out of 10, Exceptional, (6 reviews)
"Cute and clean place, just the right amount of room for the two of us. Great location with shops, cafes, and the river right around the corner."
United States
Kelly O.
$193 nightly
The price is $218
Oct 20 - Oct 21
Total with taxes and fees
Deluxe Cute Apt | 1min Walk Restaurants + Shops
A staircase with white steps and dark risers, leading to a door at the top.

19. 2 bedrooms that are warm and comfortable queen size beds

2 bedrooms that are warm and comfortable queen size beds
Williston North
8.8 out of 10, Excellent, (24 reviews)
"This was a perfect 2 bedroom apartment for our needs in a house with grassy yard. It was 5-10 minutes from Burlington and a convenient location, big driveway for parking. Great bagel place Green Mountain Bagels up the street. Everything was very clean and extremely comfortable. Errin was very attentive made sure the check in process was easy; and offered any assistance, which we did not need! Would recommend!"
United States
Laura W.
$197 nightly
The price is $223
Oct 18 - Oct 19
Total with taxes and fees
2 bedrooms that are warm and comfortable queen size beds
An outdoor patio with wooden flooring, two metal chairs, and a table.

20. The Hideaway

The Hideaway
Hinesburg
9.0 out of 10, Wonderful, (19 reviews)
"Easy check in and perfect amenities for our trip!"
United States
Zac B.
$134 nightly
The price is $150
Oct 18 - Oct 19
Total with taxes and fees
The Hideaway
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 Devlin

The Devlin

8/10 Good
"Wonderful hotel, friendly staff and great location. Breakfast is a misnomer. Coffee and some processed food in plastic wrappers. Go out for breakfast."
Maurice 1-night trip
Posted 1 hour ago
The Devlin

Find out more about Town of Chesterfield

Discover your perfect Town of Chesterfield vacation rental with Expedia

How many vacation rentals are available in Town of Chesterfield?


Expedia has plenty of vacation rentals to choose from in and around  Town of Chesterfield, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Town of Chesterfield?


The selection of Town of Chesterfield vacation rentals we have selected for you start as low as $133 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Town of Chesterfield?


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Why should I choose a vacation rental in Town of Chesterfield?


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How do I find the best deal on a vacation rental in Town of Chesterfield?


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What amenities are available in a vacation rental in Town of Chesterfield?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Town of Chesterfield vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Town of Chesterfield?   


Everytime is a great time to head to Town of Chesterfield! Staying in a Town of Chesterfield vacation rentals you will always find lots going on to keep you entertained. 


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Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Town of Chesterfield vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.