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Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (169 reviews)
"3rd year at this listing, absolutely love it. Close to okemo and mount snow. Host got back to me very quickly when reached out to. "
United States
Jake D.
The price is AED 624
AED 1,312 total
includes taxes & fees
14 May - 15 May
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is AED 225
AED 1,151 total
includes taxes & fees
12 May - 13 May
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Property grounds

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (30 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is AED 180
AED 814 total
includes taxes & fees
12 May - 13 May
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is AED 582
AED 1,079 total
includes taxes & fees
12 May - 13 May
Family Friendly Hilltop House In Putney Vermont
Exterior

Two Double bed Hotel Room with outdoor heated pool 216

Two Double bed Hotel Room with outdoor heated pool 216
Killington
The price is AED 300
AED 480 total
includes taxes & fees
12 May - 13 May
Two Double bed Hotel Room with outdoor heated pool 216
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is AED 822
AED 1,004 total
includes taxes & fees
12 May - 13 May
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Interior

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Ludlow
9.8 out of 10, Exceptional, (85 reviews)
"Great proximity to mountain and Ludlow downtown area."
United States
Yasmine O.
The price is AED 413
AED 1,126 total
includes taxes & fees
12 May - 13 May
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route
Property grounds

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Ludlow
9.8 out of 10, Exceptional, (108 reviews)
"We enjoyed our stay, the house was lovely and close to everything in Ludlow and Okemo."
United States
Hannah M.
The price is AED 413
AED 1,114 total
includes taxes & fees
13 May - 14 May
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Exterior

Two Double Bed Standard Hotel Room with outdoor heated pool 101

Two Double Bed Standard Hotel Room with outdoor heated pool 101
Killington
8.2 out of 10, Very Good, (17 reviews)
"Loved this lodging. Super fun outdoorsy place. Enjoyed the warm pool and grills and picnic table area. Liked the coffee in mornings in the office. "
United States
Dr Arun
The price is AED 300
AED 481 total
includes taxes & fees
12 May - 13 May
Two Double Bed Standard Hotel Room with outdoor heated pool 101
Exterior

Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209

Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209
Killington
8.8 out of 10, Excellent, (14 reviews)
"Our experience was easy and relaxing. It was nice and close to Killington Mountain and everything that we needed for the weekend was available."
United States
Parker D.
The price is AED 382
AED 578 total
includes taxes & fees
12 May - 13 May
Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209
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 Chester Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"I booked a last minute reservation and was very pleasantly surprised. The hotel is beautiful! My room was large and I had a porch that looked out into a small pond and a park that had picnic tables. There were many areas throughout the hotel to socialize, including an outdoor area with a fire pit. Large game room in the second floor. Indoor pool on the ground level. Staff were friendly and professional. Highly recommend!"
Jane 2-night trip
Posted 4 days ago
On The River Inn

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Frequently asked questions

Searching for romantic hotels in Chester?
If you and your partner need some romantic time away, we've got just the thing. Our guests also enjoy Chester for its shopping, coffeehouses, and skiing. If you want to explore the area, you might head to DaVallia Art & Accents or Bonnie's Bundles Dolls. If you're interested in staying near a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list.
What's the best place to stay for a romantic getaway to Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favorite guesthouse for couples, and features free WiFi and a garden.
When is the best time of year for a romantic getaway to Chester?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Chester: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What is there to do in Chester?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all that Chester has to offer. Couples looking for a little of everything will enjoy Chester for its coffeehouses, restaurants, and skiing. You might consider a stop at DaVallia Art & Accents or Bonnie's Bundles Dolls while you're out and about.
What's the best way to get to Chester and around town during my romantic getaway?
These transportation options in Chester might help your romantic trip go off without a hitch: The closest major airport is Springfield, VT (VSF-Hartness State), located 6.6 mi (10.7 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip.