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Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

Interior

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
10.0 out of 10, Exceptional, (71 reviews)
"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
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, (27 reviews)
"Great cozy hotel very close to Mount Snow. "
United States
Yuhui
The price is AED 484
AED 532 total
includes taxes & fees
20 Jan - 21 Jan
Hideaway Inn Mt. Snow
Pub

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown
3.0 star property
Keene
8.8 out of 10, Excellent, (1,002 reviews)
"Very comfortable and clean."
United States
Christina
The price is AED 661
AED 717 total
includes taxes & fees
26 Jan - 27 Jan
Courtyard by Marriott Keene Downtown
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very Good, (843 reviews)
"Room was very clean and the hotel staff were very friendly! Hotel is attached to a movie theater which is great!"
United States
Jaime
The price is AED 475
AED 522 total
includes taxes & fees
20 Jan - 21 Jan
Latchis Hotel
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, (636 reviews)
"Scenic balcony. Friendly staff. We had a lovely stay. "
United States
Travis
The price is AED 592
AED 642 total
includes taxes & fees
26 Jan - 27 Jan
Riverside Hotel, an Ascend Collection Hotel
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (342 reviews)
"Absolutely stunning bed and breakfast! The room and facilities were clean and welcoming. We really enjoyed the decorations and details of the house. The breakfast was delicious! Will definitely be coming back next time we are in town for ski! Highly recommended staying at Colonel Williams! "
United States
Ekaterina
The price is AED 538
AED 592 total
includes taxes & fees
27 Jan - 28 Jan
Colonel Williams Inn
Property amenity

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel
3.0 star property
Manchester Center
8.4 out of 10, Very Good, (880 reviews)
"Rooms were spotless and staff was great!"
United States
Helen
The price is AED 331
AED 424 total
includes taxes & fees
25 Jan - 26 Jan
The Palmer House Resort, an Ascend Collection 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, (956 reviews)
"Nice hotel! Very friendly staff and great value compared to other accommodations. "
United States
Mauricio
The price is AED 562
AED 641 total
includes taxes & fees
28 Jan - 29 Jan
Pointe at Castle Hill Resort
Exterior

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, (785 reviews)
"My family has been staying here for 10 years. The staff is excellent. The grounds are perfect and their tons of things for my family to do while being equidistant to okemo and Killington mountains"
United States
Harold
The price is AED 547
AED 657 total
includes taxes & fees
26 Jan - 27 Jan
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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, (955 reviews)
"Every thing was excellent "
United States
James
The price is AED 659
AED 798 total
includes taxes & fees
26 Jan - 27 Jan
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

Top Chester Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Fantastic! Easy check in and out! Rooms were updated and spotless. Great customer service!"
Rianna 2-night trip
Posted 2 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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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.