Chester Hotel Guide - Romantic Hotels in Chester, Vermont

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Check availability on Chester Romantic Hotels

Tonight
28 Nov - 29 Nov
Tomorrow
29 Nov - 30 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Chester Romantic Hotels

Reception
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3.0 star property
Keene
8.8 out of 10, Excellent, (1006)
"Lovely hotel"
United States
ronald
The price is €150
includes taxes & fees
14 Dec - 15 Dec
Courtyard by Marriott Keene Downtown
Hiking
Latchis Hotel

Latchis Hotel

2.5 star property
Brattleboro
8.4 out of 10, Very good, (832)
"Great stay"
United States
Jason
The price is €124
includes taxes & fees
1 Dec - 2 Dec
Latchis 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, (776)
"Very welcoming, spacious, clean. Perfect for a family of 4. "
United States
Kathleen
The price is €99
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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, (626)
"Clean room, beautiful location"
United States
Marcie
The price is €142
includes taxes & fees
29 Dec - 30 Dec
Riverside Hotel, an Ascend Collection Hotel
Premium bedding, desk, blackout curtains, iron/ironing board
The Common Man Inn & Restaurant

The Common Man Inn & Restaurant

3.5 star property
Claremont
9.6 out of 10, Exceptional, (369)
"Wonderful place to stay "
United States
John
The price is €117
includes taxes & fees
30 Nov - 1 Dec
The Common Man Inn & Restaurant
Front of property
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
The price is €149
includes taxes & fees
30 Nov - 1 Dec
Colonel Williams Inn
Indoor pool
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 star property
Cavendish
8.8 out of 10, Excellent, (918)
"Clean room, great staff, wonderful suggestions for area restaurants and attractions."
United States
Margie
The price is €166
includes taxes & fees
30 Nov - 1 Dec
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, (935)
"Great place for the price "
United States
Karen
The price is €187
includes taxes & fees
1 Dec - 2 Dec
The Black Bear Lodge at Stratton Mountain Resort
Interior
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
The Inn at Weathersfield
Exterior
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 star property
Manchester
7.4 out of 10, Good, (571)
"Nice old Inn!"
United States
Daniel
The price is €175
includes taxes & fees
7 Dec - 8 Dec
The Equinox Golf Resort & Spa
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 Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

10/10 Excellent
"Courteous staff Clean room"
Laura 1-night trip
Posted 6 days ago
The Equinox Golf Resort & Spa

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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.