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

Town of Chesterfield Holiday Rentals

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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 NZ$792
includes taxes & fees
3 Nov - 4 Nov
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, (344 reviews)
"Had a very nice stay"
United States
David
The price is NZ$238
includes taxes & fees
8 Nov - 9 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 NZ$251
includes taxes & fees
27 Oct - 28 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, (41 reviews)
"Great location and cozy."
United States
Ken L.
The price is NZ$314
includes taxes & fees
3 Nov - 4 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, (197 reviews)
"Location was great- right across from Olympic center."
United States
Lana
The price is NZ$238
includes taxes & fees
1 Nov - 2 Nov
Lake Placid Inn Main Street
A cozy living room with a blue sofa, a coffee table, and a dining area with a table and chairs.

6. Apartment in historic farmhouse

Apartment in historic farmhouse
Milton
9.6 out of 10, Exceptional, (141 reviews)
"Great location, very quiet and the goats were fun !!"
United States
Ellen O.
The price is NZ$386
includes taxes & fees
26 Oct - 27 Oct
Apartment in historic farmhouse
A compact room with a kitchenette, a bed, a desk with a lamp, and a ceiling light fixture.

7. 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 NZ$323
includes taxes & fees
28 Oct - 29 Oct
City Nest.
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, (96 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 NZ$649
includes taxes & fees
11 Nov - 12 Nov
2 BR 3 Min Walk to Medical Center and UVM!
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.

9. 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 NZ$379
includes taxes & fees
2 Nov - 3 Nov
Cozy- 2-Bedroom clean and Quiet- Maple St. Walk anywhere
A house with a front porch, a door with a window, and a grassy yard with trees.

10. 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.
The price is NZ$372
includes taxes & fees
25 Oct - 26 Oct
Comfy, sunny, Wi-fi + coffee Walk to Downtown Winooski
A two-story house with a balcony, a patio with outdoor furniture, and a large window.

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

Swim, Boat & Explore! Lake Champlain Retreat!
3.0 star property
Malletts Bay
The price is NZ$1,223
includes taxes & fees
31 Oct - 1 Nov
Swim, Boat & Explore! Lake Champlain Retreat!
A wooden deck with a view of a forest and a cloudy sky.

12. 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 NZ$348
includes taxes & fees
11 Nov - 12 Nov
Onion City Retreat: a place to relax and rejuvenate.
A modern living room with a large flat-screen TV, a wooden coffee table, and two armchairs.

13. 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 NZ$399
includes taxes & fees
16 Nov - 17 Nov
Sweet & Cozy Studio Apartment
A modern living room with a brown sofa, a patterned rug, a ceiling fan, and a kitchen in the background.

14. 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, (46 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 NZ$497
includes taxes & fees
25 Oct - 26 Oct
NEW!! Cozy Guest House with WiFi, Coffee Bar & Sunsets
A bedroom with a bed, bedside table, lamp, and a small potted plant.

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

New Modern Studio- Hop Skip & Jump to Waterfront
Downtown Burlington
9.6 out of 10, Exceptional, (30 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 NZ$403
includes taxes & fees
28 Oct - 29 Oct
New Modern Studio- Hop Skip & Jump to Waterfront
A bedroom with a bed, a sofa, a small table, and a window.

16. Stylish Studio in the Queen City

Stylish Studio in the Queen City
Old North End
9.0 out of 10, Wonderful, (19 reviews)
"We really liked the location for our needs."
United States
Anna
The price is NZ$324
includes taxes & fees
25 Oct - 26 Oct
Stylish Studio in the Queen City
A modern kitchen with white cabinets, a built-in microwave, and a refrigerator.

17. Large cozy and peaceful apartment walk anywhere

Large cozy and peaceful apartment walk anywhere
Winooski
9.8 out of 10, Exceptional, (53 reviews)
"The house was very clean and in a quiet neighborhood. Host was very responsive. King bed was very comfortable. Well stocked with necessities- soap, shampoo, toilet paper, etc. Nice to also have parking."
United States
Shawna
The price is NZ$423
includes taxes & fees
17 Nov - 18 Nov
Large cozy and peaceful apartment walk anywhere
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
The price is NZ$326
includes taxes & fees
27 Oct - 28 Oct
Central Location, Cozy Studio with WiFi and AC in enchanting South Burlington
A two-story house with a balcony, a covered patio, and a well-maintained lawn.

19. 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, (18 reviews)
"Cute place, very clean we had all the comforts of home."
United States
Ellen
The price is NZ$468
includes taxes & fees
25 Oct - 26 Oct
Charming Studio Se7en apartment in tranquil Shelburne, perfect for your getaway!
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
The price is NZ$410
includes taxes & fees
25 Oct - 26 Oct
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

Hotel Champlain Burlington, Curio Collection by Hilton

Hotel Champlain Burlington, Curio Collection by Hilton

8/10 Good
"Beautiful property, friendly and helpful staff. The TV channels are very limited. Toilet paper is terrible."
Kathryn 3-night trip
Posted 10 hours ago
Hotel Champlain Burlington, Curio Collection by Hilton

Find out more about Town of Chesterfield

Everything you need to know about Town of Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Town of Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Town of Chesterfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Town of Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Town of Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Town of Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Town of Chesterfield holiday rentals we have selected for you start as low as NZ$233 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Town of Chesterfield rentals

At Expedia, we put the best Town of Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Town of Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Town of Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Town of Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.