Romantic Hotels & Resorts in Chester from AU$165

  • 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

Room 4

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (349 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is AU$240
includes taxes & fees
15 Mar - 16 Mar
Colonel Williams Inn
Interior

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
10.0 out of 10, Exceptional, (75 reviews)
"Everything was really lovely, clean and nice. Loved the downstairs lounge and bar areas, so warm and relaxing. The host was extremely gracious. Looking forward to going back soon! "
United States
James
The Inn at Weathersfield
Property amenity

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
8.8 out of 10, Excellent, (69 reviews)
"Clean cozy rooms, overall good stay"
United States
Wade
The price is AU$210
includes taxes & fees
11 Mar - 12 Mar
Hideaway Inn Mt. Snow
Interior entrance

The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (378 reviews)
"We loved staying here! It is very quaint, everyone is friendly and the restaurant is great!"
United States
Erica
The price is AU$232
includes taxes & fees
15 Mar - 16 Mar
The Common Man Inn & Restaurant
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, (810 reviews)
"Big, clean, friendly, great "
United States
Brian
The price is AU$199
includes taxes & fees
12 Mar - 13 Mar
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
American cuisine

The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
4.0 star property
Manchester Village Historic District
9.8 out of 10, Exceptional, (354 reviews)
"Great room, nice staff."
United States
Gary
The price is AU$263
includes taxes & fees
12 Mar - 13 Mar
The Reluctant Panther Inn and Restaurant
Sun deck

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel
2.5 star property
West Chesterfield
9.6 out of 10, Exceptional, (640 reviews)
"Scenic balcony. Friendly staff. We had a lovely stay. "
United States
Travis
The price is AU$236
includes taxes & fees
9 Apr - 10 Apr
Riverside Hotel, an Ascend Collection Hotel
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (853 reviews)
"Great room, friendly & helpful staff, plus a great location in the community"
United States
Jude
The price is AU$165
includes taxes & fees
12 Mar - 13 Mar
Latchis Hotel
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, (1,005 reviews)
"Friendly staff, clean rooms. "
United States
Kirt
The price is AU$210
includes taxes & fees
24 Mar - 25 Mar
Pointe at Castle Hill Resort
Free WiFi, bed sheets

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, (980 reviews)
"Very friendly staff, excellent location. Breakfast was great and room was just what we needed"
United States
Val
The price is AU$231
includes taxes & fees
1 Apr - 2 Apr
The Black Bear Lodge at Stratton Mountain 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

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Top Chester Hotel Reviews

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Great location, most convenient hotel , everything is perfect. "
Weishuang 2-night trip
Posted 7 hours ago
The Black Bear Lodge at Stratton Mountain Resort

Frequently asked questions

Searching for romantic hotels in Chester?
If you and your partner need some romantic time away, we'd like to help you plan for it. Couples choose Chester for its coffee shops 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 lounge around in luxurious bedding 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 hotel for couples in Chester?
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favourite guest house 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, take a look at these details about year-round temperatures in Chester: The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.
What is there to do in Chester?
There's nothing better than seeing 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 coffee shops, restaurants and skiing. You might consider stopping 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 get off to a smooth start: The closest major airport is in Springfield, VT (VSF-Hartness State), located 6.6 mi (10.7 km) from the city centre. If you'd like to explore around the area, consider renting a car to explore more sights.