
Town of Chesterfield Vacations & Trips from $687
Book a Hotel + Flight or Car together to unlock savings
Top destinations in Town of Chesterfield

Keeseville
The Latest Town of Chesterfield Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Grunberg Haus Inn & Cabins
Save 100% on your flight
Price was $971, price is now $687 per person
$687
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Burlington (BTV)
10/10 Exceptional! (13 reviews)
This is our second time staying at Grunberg Haus and we will absolutely be back again. Hospitality is unmatched and there is lots to do in the surrounding area.
Reviewed on Aug 11, 2025

Club Wyndham Smugglers’ Notch Vermont
Save 100% on your flight
Price was $1,148, price is now $778 per person
$778
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Burlington (BTV)
8.4/10 Very Good! (196 reviews)
One of our favorite trips. We come once a year. Amenities are awesome. The area is great. Quite a distance from other areas but that is literally the only downfall. The rooms are amazing. Pool is always clean.
Reviewed on Sep 22, 2025

Green Mountain Inn
Save 100% on your flight
Price was $1,191, price is now $821 per person
$821
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Burlington (BTV)
9.4/10 Exceptional! (1,007 reviews)
Beautiful setting. Quaint & historic inn. Conveniently within walking distance to restaurants, shopping, etc. Clean, comfortable, cozy rooms. Outstanding staff. Two restaurants on property with varied menus.
Reviewed on Sep 27, 2025

Smugglers' Notch Resort Private Suites
Save 100% on your flight
Price was $1,458, price is now $1,022 per person
$1,022
per person
Oct 30 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Burlington (BTV)
7.8/10 Good! (19 reviews)
Located in a nice place, but just be informed - this is a privately owned property by wrote task (not a Smuggler’s notch property).
Expedia does not mention this while booking. Expedia also misguides when it says you will have access to all the resort amenities.
It was shocking to find out after a non-refundable booking that a separate company owns Telemark rentals, and that it is not associated with Smuggler’s notch. That can be a deal breaker for many. Address provided was 1.5 miles away from the actual location. Terrible experience with that. Also, check-in time is 5 pm (not 4), and they charge you security deposit after you book. Very surprising.
Property itself was good. No complaints about it.
Reviewed on Sep 2, 2025

Residence Inn by Marriott, North Conway
Settlers Green
Save 100% on your flight
Price was $1,018, price is now $716 per person
$716
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip flight included
New York (JFK) to Burlington (BTV)
9.4/10 Exceptional! (1,002 reviews)
Overall experience was amazing especially loved the pool and hot tub - just what we needed! Thank you for a lovely stay!
Reviewed on Sep 21, 2025
Town of Chesterfield Hotel Deals

Green Mountain Suites Hotel
401 Dorset St, South Burlington, VT
$167 nightly
The price is $184 total per night from Oct 26 to Oct 27
$184 total
Oct 26 - Oct 27
Total with taxes and fees
9.4/10 Exceptional! (1,550 reviews)
"Very comfortable bed"
Reviewed on Sep 21, 2025

DoubleTree by Hilton Burlington Vermont
870 Williston Rd, South Burlington, VT
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $203 total per night from Oct 26 to Oct 27
$203 total
Oct 26 - Oct 27
Total with taxes and fees
8.8/10 Excellent! (1,902 reviews)
"Breakfast was fresh. However menu can be changed to provide more variety."
Reviewed on Sep 25, 2025

High Peaks Resort
2384 Saranac Ave, Lake Placid, NY
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $153 total per night from Oct 26 to Oct 27
$153 total
Oct 26 - Oct 27
Total with taxes and fees
9.2/10 Wonderful! (1,010 reviews)
Gorgeous place
"Beautiful hotel in an excellent location. Walk to everything like restaurants, shopping and the lake. The service was great and a really good restaurant. Beautiful views from our room. We’ll be back."
Reviewed on Sep 19, 2025
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.
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Other vacations you might like
- Top cities in Town of Chesterfield
- Vacations and getaways similar to Town of Chesterfield
- Best vacation destinations by month
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.