Beginning of main content
Customized for your search:

Cheap Hotels in Chester, Vermont

Chester hotels

Choose from 7 Chester Hotel Deals

Inn Victoria - Chester Hotels
Rating: 4.0 Stars

Inn Victoria

321 Main St, Chester - Map
"Nice hotel close to skiing"
Stayed only one night, but was very satisfied. I would definitely go back.
A Traveller
Situated in Chester, this bed & breakfast is 0.3 mi (0.5 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 …More
The Karass Inn - Chester Hotels
Rating: 3.0 Stars

The Karass Inn

225 Pleasant Street, Chester - Map
"A short trip to Vermont"
The stay at the Karass Inn was pleasant. It was short but comfortable and the staff was very friendly and helpful. The complimentary Breakfast was equivalent to a 5 Star Restaurant. I would stay there again for my next trip to Vermont.
Traveller from Elverson, PA
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 …More
Motel in the Meadow - Chester Hotels
Rating: 2.5 Stars

Motel in the Meadow

936 VT Route 11 West, Chester - Map
"Quaint clean motel close enough to Okemo Mountain."
The motel was clean and very quaint. I would return when I plan another ski weekend at Okemo Mountain. Heat worked well and beds comfortable. Warm homemade muffins and hot coffee offered a great start to each morning. Relaxing 20 min drive to ski resort was no problem. At night a restaurant/bar a few doors down was very convenient and food was good.
Traveller from nj
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 …More
Hugging Bear Inn and Shoppe - Chester Hotels
Rating: 2.5 Stars

Hugging Bear Inn and Shoppe

244 Main Street, Chester - Map
Great place, very clean. Owner pleasant and efficient
A Traveller
Situated in Chester, this bed & breakfast is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 …More
Chester House Inn - Chester Hotels
Rating: 3.0 Stars

Chester House Inn

266 Main St, Chester - Map
"Felt right at home"
Innkeeper Bob made us feel right at home at Chester House Inn. A classic New England style inn with all the charm and history you could want. Plus a tasty breakfast and perfect location for winter sports!
Traveller from Massachusetts
Situated in Chester, this bed & breakfast is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 …More
Rose Arbour Bed & Breakfast - Chester Hotels
Rating: 2.5 Stars

Rose Arbour Bed & Breakfast

55 School Street, Chester - Map
"Small town charm"
We really enjoyed our stay at the Rose Arbour B&B! The house is old so there are definitely some creaky floorboards and doors that stick, so if you're someone who needs everything to be absolutely perfect this probably isn't the place for you. If, like me, you enjoy the charm of staying in a historic, homey victorian and are more than happy to put up with the little quirks that come along with it, then you'll be very happy here! FYI, the owner has 4 dogs! They were extremely friendly and well-behaved, and are always kept in the owners private quarters, so if you're allergic or deathly afraid of dogs it may not be the place for you. The breakfast was delicious and the dining area is the perfect cozy place to enjoy your morning coffee and apple cinnamon pancakes, lemon creme french toast, or whatever other delicacy the host is serving.
A Traveller
Situated in the historical district, this bed & breakfast is 0.2 mi (0.4 km) from Vermont Institute of Contemporary Arts and …More
Fullerton Inn - Chester Hotels
Rating: 2.5 Stars

Fullerton Inn

40 The Common, Chester - Map
"Classic Vermont Inn close to Okemo + great food"
Booked this mostly because of the overall value and proximity to Okemo for skiing. Upon our return from Okemo, my buddy & I stopped in the tavern for a drink. It turned into a flight of Vermont beers, wings, and then dinner, all next to a fireplace loaded with hot coals. With food and atmosphere like that, there was little motivation to try anywhere else. The room was comfy, clean and relatively small but fine for two guys with ski gear. Breakfast (continental "plus") did not disappoint with fresh fruit, waffles, scones, hot coffee, etc.
Traveller from Chalfont, PA
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 …More

Search from 7 Chester Hotels

    Why book with Hotwire ?

    • Price Guarantee
    • No Hotwire Cancellation Fee
    • 91% customer satisfaction

    Chester is calling — find the perfect hotel

    Everyone wants to score a deal on travel, but price is just one factor to consider when booking an unforgettable hotel. Whether you’re visiting family, attending a conference or taking a well-earned vacation in Chester, having an awesome experience should be a no-brainer.

    Hotwire will hook you up! From restful nights near your flight to that prime spot in the city’s heart, we’ve done our research to bring the best options to your fingertips. Book your Chester hotel with us now and start your next adventure.

    You’re not the average traveler — and we know it

    You’ve done your homework and know exactly where you want to go. We’re here to help with some Hotwire travel geek-approved tips on how to save on your booking.

    Get away for the weekend

    Hotels in bigger cities usually charge higher rates during the week, when people are traveling for business. Weekends can be a bargain! It’s the other way around for vacation spots, so if you’re looking for a beach escape, consider a mid-week trip.

    Give yourself some wiggle room

    If your plans are flexible, play around with some different travel dates – a shift of a few days either way can help you save big. Prices usually jump the weekends before and after popular holidays, so we recommend steering clear of them. Or consider visiting during the off-season, when prices are generally lower.

    Plan around big events

    Are prices surprisingly high? There might be a huge conference or festival in town. Consider shifting your dates if you can. Of course, if that’s why you’re going, you’ll have to bite the bullet. We’ll still work to get you the best rates out there.

    Noodle over new adventures

    Set aside time to plan what you want to see, taste and discover. Nothing completes a trip, big or small, like a few new experiences! Check city apps or area websites to find out what’s new and what events are happening during your stay. Even during a family reunion, you can detour to that locals-only fish taco stand or under-the-radar music club. Your cousins will be impressed.