Find Romantic Hotels in Chester, VT from $134

Start date: Check-in selected.
To Date
End date: Check-out

Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

Interior
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
10.0 out of 10, Exceptional, (2)
"Tout y était!"
Canada
Martin
$149 nightly
The price is $164
Dec 14 - Dec 15
Total with taxes and fees
Hideaway Inn Mt. Snow
Interior
The Inn at Weathersfield

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (70)
"The location of the Inn was in an area that was just wonderful. Staff was very friendly and the menu options were very tasty. Room was clean and well maintained. "
United States
Joshua
$211 nightly
The price is $230
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Inn at Weathersfield
Exterior
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0 star property
Brownsville
9.0 out of 10, Wonderful, (777)
"Very welcoming, spacious, clean. Perfect for a family of 4. "
United States
Kathleen
$134 nightly
The price is $146
Dec 15 - Dec 16
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Sundeck
Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (628)
"Clean room, beautiful location"
United States
Marcie
$161 nightly
The price is $175
Dec 17 - Dec 18
Total with taxes and fees
Riverside Hotel, an Ascend Collection Hotel
Free WiFi, bed sheets
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.6 out of 10, Good, (940)
"We like that getting to Stratton Mountain and the downtown area was very walkable or easy to get there by regularly running shuttle buses."
United States
Mark
$185 nightly
The price is $204
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
Premium bedding, desk, blackout drapes, iron/ironing board
The Common Man Inn & Restaurant

The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (370)
"Great place to stay! "
United States
Candace M
$139 nightly
The price is $151
Dec 14 - Dec 15
Total with taxes and fees
The Common Man Inn & Restaurant
Indoor pool
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (923)
"Great place to stay while skiing at okemo"
United States
Ken
$144 nightly
The price is $157
Dec 11 - Dec 12
Total with taxes and fees
Pointe at Castle Hill Resort
Exterior
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa
4.5 star property
Manchester
7.4 out of 10, Good, (576)
"Nice old Inn!"
United States
Daniel
$215 nightly
The price is $236
Dec 11 - Dec 12
Total with taxes and fees
The Equinox Golf Resort & Spa
Front of property
Colonel Williams Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
$146 nightly
The price is $161
Dec 14 - Dec 15
Total with taxes and fees
Colonel Williams Inn
Reception
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1004)
"Very comfortable and clean."
United States
Christina
$180 nightly
The price is $195
Dec 17 - Dec 18
Total with taxes and fees
Courtyard by Marriott Keene Downtown
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.
View all properties

Top Chester Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Great place to stay while skiing at okemo"
Ken 1-night trip
Posted 4 days ago
Pointe at Castle Hill Resort

Frequently asked questions

Searching for romantic hotels in Chester?
If you and your partner need a romantic vacation, we'd like to help you plan for it. Couples choose Chester for its coffeehouses and restaurants. During your trip, you might consider a visit to DaVallia Art & Accents or Bonnie's Bundles Dolls while you're exploring Chester with your significant other. Whether you'd like to sip a glass of champagne or get a couples' massage, you'll be sure to find accommodation in Chester to make for the perfect couples' getaway.
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.

Explore a world of travel with Expedia