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Cheap Hotels in Chester, Vermont

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Choose from 50 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
Jackson Gore Inn - Ludlow Hotels
Rating: 3.0 Stars
$182

Jackson Gore Inn

111 Jackson Gore Road, Ludlow - Map
 
 
"Nice apt. Right by the lifts"
I was upgraded to a 1-bedroom suite for no charge. It was a great trip and the facility helped make that happen.
Traveller from Sosset ny
This Ludlow condo is in the mountains, offering ski-in/ski-out access within 3 mi (5 km) of Okemo Valley Golf Club and Okemo …More
The Upper Pass Lodge at Magic Mountain - Londonderry Hotels
Rating: 2.5 Stars
$79

The Upper Pass Lodge at Magic Mountain

420 Magic Mountain Access Road, Londonderry - Map
 
 
"Nice hotel room for the price."
Room was clean, staff was friendly, dinner was great; I'd go back.
Traveller from Boston
Conveniently near skiing facilities, this Londonderry motel is located in the mountains within 3 mi (5 km) of Magic Mountain …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
Pointe at Castle Hill Resort - Proctorsville Hotels
Rating: 3.5 Stars

Pointe at Castle Hill Resort

2940 State Route 103, Proctorsville - Map
 
 
"Great option near Okemo"
Clean, comfortable, and quiet. Large rooms. Easy to get to Okemo.
A Traveller
Situated in a rural location, this spa hotel is within 9 mi (15 km) of Dorsey Park, Okemo Mountain Ski Resort, and Buttermilk …More
Castle Hill Resort And Spa - Proctorsville Hotels
Rating: 3.5 Stars

Castle Hill Resort And Spa

2940 Route 103, Proctorsville - Map
 
 
"Great for ski weekend at Okemo"
Came with 2 adults and 4 kids and stayed in a condo. Reserved a 2BR but got upgraded to a 3BR (without asking). Condo was really nice with higher-end finishes like crown moldings, nice furniture, etc. Kitchen supplies need an upgrade in this unit; for instance there was no spatula and the frying pans were all a bit of a mismatch. Owner probably needs to simply take a little inventory of supplies. Nevertheless, this was minor and we made due as usual in ski rentals! Great WiFi in the unit. 5-8 mins drive to the mountain. There is a pool and hot tub in the hotel, which is a short walk/drive down the hill. I was with my buddy and our kids and we could have easily brought our wives and other kids and still would not have felt crowded. There is a loft that could easily fit an air mattress as well. Overall a great place to stay and we will stay again. Thanks!
Traveller from New York, NY
Located near the slopes, this Proctorsville resort is within 6 mi (10 km) of Dorsey Park and Okemo Mountain Ski Resort and …More
The Karass Inn - Chester Hotels
Rating: 3.0 Stars

The Karass Inn

225 Pleasant Street, Chester - Map
 
 
"Comfy and tasty getaway."
We booked a quick last minute get away and were delighted with this Inn. It was a reasonable price with a delicious breakfast of frittatas, pancakes and bacon. The room simple and comfortable. Staff were professional and friendly but not intrusive. Parking great and location is just on the edge of the town of Chester making it walkable to the downtown for the more energetic. There is also a pizza closeby.
A Traveller
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
Swiss Inn & Restaurant - Londonderry Hotels
Rating: 2.5 Stars

Swiss Inn & Restaurant

249 Route 11, Londonderry - Map
 
 
"Convenient with dinning and bar onsite "
The place is advertised correctly. Nothing fancy but clean, friendly and convenient. Joe made the check in easy then served us great drinks and dinner at the bar then he was up early and serving us a full breakfast. I have celiac and allergic to seafood and he was able to accomodate. Plenty of parking and close to multiple ski destinations. He has plenty of books and games if you want to hang in and relax by the fire. The hot rum drinks were perfect after a day of skiing. The walls are thin but guest were quiet. We didn't use the tennis court out back so not sure if they still use them. It was covered in snow. Nice people, I would stay again. Locals also frequent. Enjoy your trip. I have nothing else to say but required to type more more more more more more more more more more
A Traveller
Situated in Londonderry, this inn is 0.5 mi (0.8 km) from Taylor Farm and within 6 mi (10 km) of Viking Nordic Center and …More
Hartness House Inn - Springfield Hotels
Rating: 3.0 Stars

Hartness House Inn

30 Orchard Street, Springfield - Map
 
 
"Beautiful mansion in Vermont"
Positives: amazing breakfast, interesting building, great staff. Negatives:cold room that's unfinished with a hallway smelling badly, tiny little fitness center with no weights, and in need of a facelift due to super dated furniture, and horrible pillows. It has tremendous potential but, needs work.
Traveller from Boston
Situated in the business district, this romantic inn is within 6 mi (10 km) of Eureka Schoolhouse, Baltimore Covered Bridge …More
The Putney Inn - Putney Hotels
Rating: 2.5 Stars

The Putney Inn

57 Putney Landing Rd, Putney - Map
 
 
"no longer a quaint Inn!"
We stayed here 5 years ago. Then the rooms needed updating but it still felt like a nice country inn. The restaurant was open in the old farm house and the food was very good. The staff was very friendly and informational about the area. Now, the rooms have been redone and are very nice and clean but no longer have the country inn feel - modern and like any hotel. Sadly, the old farm house is closed and in bad disrepair. There was no restaurant, only a continental breakfast in the small office area. It was sad to see. We did enjoy our visit and the price was very reasonable for a nice room.
Traveller from MA
Situated in Putney, this motel is 0.4 mi (0.6 km) from Yellow Barn and within 9 mi (15 km) of United States Navy Seabee …More

Search from 50 Chester Hotels


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    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.

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