Find Romantic Hotels in Chester, VT from CA $178

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Check availability on Chester Romantic Hotels

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Our top choices for Chester romantic hotels

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)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is CA $231
CA $502 total
includes taxes & fees
May 4 - May 5
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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 CA $67
CA $300 total
includes taxes & fees
May 3 - May 4
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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 CA $196
CA $379 total
includes taxes & fees
May 3 - May 4
Family Friendly Hilltop House In Putney Vermont

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)
"Perfect spot for Mount Snow "
United States
Bobby
The price is CA $83
CA $429 total
includes taxes & fees
May 3 - May 4
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Two Double bed Hotel Room with outdoor heated pool 216

Two Double bed Hotel Room with outdoor heated pool 216
Killington
The price is CA $111
CA $178 total
includes taxes & fees
May 10 - May 11
Two Double bed Hotel Room with outdoor heated pool 216

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 CA $304
CA $376 total
includes taxes & fees
May 3 - May 4
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

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)
"We had a great stay at this home for a long weekend skiing at Okemo. "
United States
Lisa W.
The price is CA $153
CA $417 total
includes taxes & fees
May 3 - May 4
Beautiful Village Home, Short Walk to Restaurants, Shops, On Shuttle Route

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 CA $111
CA $178 total
includes taxes & fees
May 10 - May 11
Two Double Bed Standard Hotel Room with outdoor heated pool 101

107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool

107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Killington
8.0 out of 10, Very good, (7 reviews)
"Efficient and affordable option for a short stay."
United States
Marnie O.
The price is CA $111
CA $178 total
includes taxes & fees
May 31 - Jun 1
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
7.4 out of 10, Good, (21 reviews)
"Poor management company. Great lodge. "
United States
Billy W.
The price is CA $181
CA $526 total
includes taxes & fees
May 3 - May 4
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
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.

Top Chester Hotel Reviews

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.

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