Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Save up to $603 by booking Flight + Hotel.

Search 321,000 hotels and 400 airlines worldwide.

Get the price Guarantee available for your trip.


Chester

Considering a Chester vacation? It's time to start organizing.

Packages in Chester

Expedia has flight and lodging packages for you. We like to reduce your stress by pairing up your lodging and flight bookings to save you even more money. Just think of all the things you can do in Chester with the extra cash.

Don't you think it would be nice to save up to $603? Get your group's travel package today!

Our comprehensive international database allows you to research 321,000 hotels worldwide and up to 400 partner airlines, and it additionally rewards you with discounts.

For Chester getaways, you'll have a difficult time topping Expedia's package deals.

You never have to worry about altering your plans, as we do not charge additional cancellation fees for almost all of our reservations.

Chester Vacation Packages

From Chester, it is roughly 55 miles east to Concord and 70 miles north to Montpelier.

Make time for a Proctorsville side trip. This location is merely 9 miles to the north and has Okemo Mountain Ski Resort.

There is little else that restores the soul like a trip to the ocean. Pack a picnic, buy your favorite wine and bask in the lovely scenery of Million Dollar Beach, 55 miles west from Chester. Another wonderful place is Endicott Rock Park, 60 miles to the northeast.

Many travelers visit this part of Central Vermont- Killington for its beloved natural surroundings. Find out what it's all about at Chesterfield Gorge Natural Area and Madame Sherri Forest, 25 miles and 30 miles away from Chester, respectively.

Put on some warm socks and hit the trails at the resorts near Chester. Pats Peak and Ragged Mountain Ski Resort are 40 miles and 40 miles away, respectively.

Make sure you stop at Vermont Institute of Contemporary Arts or DaVallia Art & Accents.

Rutland Southern Vermont Regional Airport is the closest airport at about 25 miles to the northwest, so just make sure you leave plenty of time.

Chester has hotel rooms, suites and apartments for all types of vacationers. With Expedia's booking page, visitors can take their pick from 5 Chester hotel listings.

The Hugging Bear Inn and Shoppe and Rose Arbour Bed & Breakfast are among the best lodgings in Chester.


Top Hotel Deals

See all 85 Hotels in Chester
$77
Motel in the Meadow

Motel in the Meadow

936 VT Route 11 West, Chester
4.0
of 5, from 7 reviews
2.5 out of 5.0

Situated in Chester, this motel is 1.7 mi (2.7 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

$129
Fullerton Inn

Fullerton Inn

40 The Common, Chester
4.0
of 5, from 7 reviews
2.5 out of 5.0

Situated in Chester, this inn is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

$119
The Karass Inn

The Karass Inn

225 Pleasant Street, Chester
5.0
of 5, from 6 reviews
3.0 out of 5.0

Situated in a state park, this bed & breakfast is 0.7 mi (1.1 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

$140
Inn Victoria

Inn Victoria

321 Main St, Chester
4.8
of 5, from 8 reviews
4.0 out of 5.0

Situated in Chester, this bed & breakfast is 0.3 mi (0.5 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

$149
Chester House Inn

Chester House Inn

266 Main St, Chester
4.1
of 5, from 13 reviews
3.0 out of 5.0

Situated in Chester, this bed & breakfast is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

$139
Hugging Bear Inn and Shoppe

Hugging Bear Inn and Shoppe

244 Main Street, Chester
4.2
of 5, from 13 reviews
2.5 out of 5.0

Situated in Chester, this bed & breakfast is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

$85
Rose Arbour Bed & Breakfast

Rose Arbour Bed & Breakfast

55 School Street, Chester
3.7
of 5, from 18 reviews
2.5 out of 5.0

Situated in the historical district, this bed & breakfast is 0.2 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont Museum of Mining and Minerals. Grafton Valley Arts Guild Cricketers Gallery and Hunter Gallery of Fine Art are also within 9 mi (15 km).

$49
The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

420 Magic Mountain Access Road, Londonderry
4.0
of 5, from 66 reviews
2.5 out of 5.0

Conveniently near skiing facilities, this Londonderry motel is located in the mountains within 3 mi (5 km) of Magic Mountain Ski Resort, Viking Nordic Center, and Lowell Lake State Park. Taylor Farm and Mill Museum are also within 9 mi (15 km).

Top Deals on Flights

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.