Chester Hotel Guide - Romantic Hotels in Chester, Vermont

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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
9.8 out of 10, Exceptional, (70 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
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)
"Very comfortable and clean."
United States
Christina
The price is €168
includes taxes & fees
25 Jan - 26 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 €123
includes taxes & fees
22 Jan - 23 Jan
Latchis 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 €149
includes taxes & fees
26 Jan - 27 Jan
Colonel Williams Inn
Property amenity

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
8.8 out of 10, Excellent, (24 reviews)
"Great cozy hotel very close to Mount Snow. "
United States
Yuhui
The price is €128
includes taxes & fees
20 Jan - 21 Jan
Hideaway Inn Mt. Snow
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, (635 reviews)
"Scenic balcony. Friendly staff. We had a lovely stay. "
United States
Travis
The price is €150
includes taxes & fees
22 Jan - 23 Jan
Riverside Hotel, an Ascend Collection Hotel
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, (782 reviews)
"Clean room, very nice staff, everything was excellent! "
United States
Karen
The price is €154
includes taxes & fees
26 Jan - 27 Jan
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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, (877 reviews)
"Rooms were spotless and staff was great!"
United States
Helen
The price is €99
includes taxes & fees
22 Jan - 23 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, (954 reviews)
"Nice hotel! Very friendly staff and great value compared to other accommodations. "
United States
Mauricio
The price is €185
includes taxes & fees
19 Jan - 20 Jan
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, (954 reviews)
"Every thing was excellent "
United States
James
The price is €192
includes taxes & fees
19 Jan - 20 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.
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Top Chester Hotel Reviews

The Manchester View

The Manchester View

10/10 Excellent
"Excellent "
Rebecca 2-night trip
Posted 1 day ago
The Manchester View

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 Bonnie's Bundles Dolls or DaVallia Art & Accents 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 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 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.