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

Holiday Rentals in Town of Chesterfield

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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 €372
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 €158
includes taxes & fees
3 Sept - 4 Sept
Little downtown gem with parking
Room

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 €229
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 €221
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 €233
includes taxes & fees
7 Sept - 8 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 €155
includes taxes & fees
2 Sept - 3 Sept
Lakeside Cottage #303 at Valcour Cottages
Private kitchen

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 €160
includes taxes & fees
14 Sept - 15 Sept
Central Location, Cozy Studio with WiFi and AC in enchanting South Burlington
Private kitchen

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 €204
includes taxes & fees
2 Sept - 3 Sept
City Chic 1BR Escape - Winooski
Living area

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 €276
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 €230
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 €255
includes taxes & fees
2 Sept - 3 Sept
2Bed Apt 5mins to i89, parking, close to dwntwn!
Living area

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 €205
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 €190
includes taxes & fees
7 Sept - 8 Sept
Comfy, sunny, Wi-fi + coffee Walk to Downtown Winooski
Room

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

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 €219
includes taxes & fees
2 Sept - 3 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 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 €195
includes taxes & fees
16 Sept - 17 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 €208
includes taxes & fees
9 Sept - 10 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 €276
includes taxes & fees
2 Sept - 3 Sept
Burlington Walkabout Peaceful City Retreat-Walk to EVERYTHING downtown.
Room

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.
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 3 hours ago
Vermont Suites

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Holiday Homes in Town of Chesterfield

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