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

Town of Chesterfield Holiday Rentals

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Our top choices for Town of Chesterfield holiday rentals

Property grounds

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 AU$616
includes taxes & fees
7 Sept - 8 Sept
High Peaks Haven is in the heart of Adirondack. Come enjoy with famil
Private kitchen

2. Little downtown gem with parking

Little downtown gem with parking
Old North End
9.6 out of 10, Exceptional, (37 reviews)
"Great location and cozy."
United States
Ken L.
The price is AU$252
includes taxes & fees
10 Sept - 11 Sept
Little downtown gem with parking
1 bedroom, iron/ironing board, WiFi, bed sheets

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

Private Apt w/ parking spot shrt walk to Dwntwn!
Old North End
10.0 out of 10, Exceptional, (17 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.
The price is AU$366
includes taxes & fees
22 Sept - 23 Sept
Private Apt w/ parking spot shrt walk to Dwntwn!
Exterior detail

4. Midcentury modern meets Vermont comfort and hospitality!

Midcentury modern meets Vermont comfort and hospitality!
South Burlington
9.0 out of 10, Wonderful, (18 reviews)
"Nice place to stay for a night or two."
United States
William H.
The price is AU$351
includes taxes & fees
2 Sept - 3 Sept
Midcentury modern meets Vermont comfort and hospitality!
Living area

5. 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 AU$398
includes taxes & fees
28 Sept - 29 Sept
Downtown Designer Digs
Property grounds

6. Lakeside Cottage #303 at Valcour Cottages

Lakeside Cottage #303 at Valcour Cottages
Plattsburgh
9.2 out of 10, Wonderful, (12 reviews)
"Sweet little cottage, well cared for and clean. The cottages have a nice outdoor gathering space on the lake."
United States
CHARLOTTE
The price is AU$247
includes taxes & fees
2 Sept - 3 Sept
Lakeside Cottage #303 at Valcour Cottages
Coffee/tea maker, fridge, microwave, oven

7. 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
10.0 out of 10, Exceptional, (11 reviews)
"Stayed for two nights, had a wonderful time! "
United States
JFimmers
The price is AU$255
includes taxes & fees
14 Sept - 15 Sept
Central Location, Cozy Studio with WiFi and AC in enchanting South Burlington
Coffee/tea maker, fridge, microwave, oven

8. City Chic 1BR Escape - Winooski

City Chic 1BR Escape - Winooski
Winooski
9.6 out of 10, Exceptional, (4 reviews)
"Cozy and nice place with everything we needed for graduation weekend. Convenient location."
United States
MICHAEL
The price is AU$325
includes taxes & fees
2 Sept - 3 Sept
City Chic 1BR Escape - Winooski
TV, fireplace

9. 1876 Winooski Getaway: Modern 2BR Victorian

1876 Winooski Getaway: Modern 2BR Victorian
Winooski
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful location and spot to stay. Thank you!!"
United States
Jen P.
The price is AU$443
includes taxes & fees
2 Sept - 3 Sept
1876 Winooski Getaway: Modern 2BR Victorian
Apartment (1 Bedroom) | Interior

10. 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 AU$372
includes taxes & fees
2 Sept - 3 Sept
2 Mi to Main Street! Cozy Burlington Guest Suite
Pool

11. 2Bed Apt 5mins to i89, parking, close to dwntwn!

2Bed Apt 5mins to i89, parking, close to dwntwn!
Winooski
10.0 out of 10, Exceptional, (14 reviews)
"Had an enjoyable stay! Felt very safe, area was quiet and peaceful. Downtown Winooski was a short drive away, as well as downtown Burlington. Beds were super comfy, unit was so much bigger than I realized. Plenty of room for 4 people (we had 2) even a great little office room away from the living room if work is needed to be done. Would def recommend and stay again"
United States
Jill K.
The price is AU$422
includes taxes & fees
2 Sept - 3 Sept
2Bed Apt 5mins to i89, parking, close to dwntwn!
Smart TV

12. Cozy Private Suite - Near BTV Airport & UVM

Cozy Private Suite - Near BTV Airport & UVM
South Burlington
9.2 out of 10, Wonderful, (10 reviews)
"Clean place, no hassle, very comfortable. I would definitely stay here again. "
United States
Robert H.
The price is AU$323
includes taxes & fees
14 Sept - 15 Sept
Cozy Private Suite - Near BTV Airport & UVM
Property grounds

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 AU$301
includes taxes & fees
7 Sept - 8 Sept
Comfy, sunny, Wi-fi + coffee Walk to Downtown Winooski
1 bedroom, desk, iron/ironing board, free WiFi

14. Stylish 1-Bed with Office • Minutes To Church St

Stylish 1-Bed with Office • Minutes To Church St
Old North End
9.4 out of 10, Exceptional, (35 reviews)
"Great location, and the host was very responsive and helpful."
United States
Jonathan B.
The price is AU$426
includes taxes & fees
2 Sept - 3 Sept
Stylish 1-Bed with Office • Minutes To Church St
Smart TV, books

15. Apartment in historic farmhouse

Apartment in historic farmhouse
Milton
9.6 out of 10, Exceptional, (137 reviews)
"Apartment was great, Chad is a good attentive Host."
United States
Bob M.
The price is AU$349
includes taxes & fees
29 Sept - 30 Sept
Apartment in historic farmhouse
Private kitchen

16. The North End Pad

The North End Pad
Old North End
9.2 out of 10, Wonderful, (25 reviews)
"Good parking and lovation"
United States
Christopher
The price is AU$260
includes taxes & fees
13 Sept - 14 Sept
The North End Pad
Gazebo

17. 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 AU$304
includes taxes & fees
8 Sept - 9 Sept
The Wilderness Inn
Outdoor dining

18. The Hideaway

The Hideaway
Hinesburg
9.0 out of 10, Wonderful, (18 reviews)
"Good setup for us, convenient and quiet location. Glad to have efficient air-conditioning as it was a very hot and humid week! Would have liked a second washcloth. (There was only one for 2 people). Rooms were clean and comfortable. Thanks!"
United States
David
The price is AU$232
includes taxes & fees
14 Sept - 15 Sept
The Hideaway
Property grounds

19. Burlington Walkabout Peaceful City Retreat-Walk to EVERYTHING downtown.

Burlington Walkabout Peaceful City Retreat-Walk to EVERYTHING downtown.
Downtown Burlington
10.0 out of 10, Exceptional, (139 reviews)
"We enjoyed our stay! The Walkabout was great. Very convenient to downtown Burlington and the water. We loved it. "
United States
Leanne H.
The price is AU$431
includes taxes & fees
2 Sept - 3 Sept
Burlington Walkabout Peaceful City Retreat-Walk to EVERYTHING downtown.
Iron/ironing board, WiFi, bed sheets

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

New Modern Studio- Hop Skip & Jump to Waterfront
Downtown Burlington
9.8 out of 10, Exceptional, (19 reviews)
"The space was even more spacious than pictured, comfortable and cozy. The location is perfect for all you could want to do in central Burlington. Will definitely stay again"
United States
Jessica V.
The price is AU$321
includes taxes & fees
9 Sept - 10 Sept
New Modern Studio- Hop Skip & Jump to Waterfront
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
"I can’t say enough good things about our room! It was extremely clean, spacious, the little kitchenette was incredibly useful, and just felt like a little home away from home. We also had issues with the tv wifi, total user error but the owners responded immediately. I would stay here again in a heartbeat."
Shannon 3-night trip
Posted 2 hours ago
Vermont Suites

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 favourite 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 depend 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 chosen for you start as low as AU$188 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.