Find Romantic Hotels in Chester, VT

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

Pub

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1,001 reviews)
"Really clean hotel, friendly staff and great location."
United States
Aaron
The price is ￥28,300
￥30,706 total
includes taxes & fees
Feb 22 - Feb 23
Courtyard by Marriott Keene Downtown
Sundeck

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (637 reviews)
"Scenic balcony. Friendly staff. We had a lovely stay. "
United States
Travis
The price is ￥23,921
￥25,955 total
includes taxes & fees
Mar 10 - Mar 11
Riverside Hotel, an Ascend Collection Hotel
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very Good, (846 reviews)
"Great room, friendly & helpful staff, plus a great location in the community"
United States
Jude
The price is ￥17,769
￥19,546 total
includes taxes & fees
Mar 9 - Mar 10
Latchis Hotel
Property amenity

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, (794 reviews)
"Good rooms"
United States
ke
The price is ￥21,854
￥26,392 total
includes taxes & fees
Feb 10 - Feb 11
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
"Room was super clean and the hosts are excellent. "
United States
Joe
The price is ￥36,884
￥40,572 total
includes taxes & fees
Feb 10 - Feb 11
Inn on Putney Road
Room 4 | Hypo-allergenic bedding, free WiFi, bed sheets

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (344 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is ￥24,514
￥26,965 total
includes taxes & fees
Feb 15 - Feb 16
Colonel Williams Inn
Sauna, aromatherapy, hot stone massages, deep-tissue massages

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (974 reviews)
"Friendly staff, clean rooms. "
United States
Kirt
The price is ￥22,850
￥26,049 total
includes taxes & fees
Mar 1 - Mar 2
Pointe at Castle Hill Resort
Front of property - evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104 reviews)
"Great stay"
United States
Wayne
The price is ￥48,336
￥52,444 total
includes taxes & fees
Feb 10 - Feb 11
Chesterfield Inn
Interior

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
10.0 out of 10, Exceptional, (72 reviews)
"Wonderful experience, Wonderful staff. Thank you!"
United States
Patrick
The Inn at Weathersfield
Exterior

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (562 reviews)
"Excellent hotel, staff well trained. "
United States
Christian
The price is ￥48,581
￥60,357 total
includes taxes & fees
Feb 22 - Feb 23
Woodstock Inn & Resort
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

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Accommodating staff"
Robert 1-night trip
Posted 4 days ago
The Black Bear Lodge at Stratton Mountain 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 Bonnie's Bundles Dolls or DaVallia Art & Accents 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 Bonnie's Bundles Dolls or DaVallia Art & Accents 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.