Find Romantic Hotels in Chester, VT

Start date: Check-in selected.
To Date
End date: Check-out

    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

Top Chester Romantic Hotels

Sundeck
Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection Hotel
2.5 star property
9.6 out of 10, Exceptional, (617)
"Loved my stay"
United States
Christine
The price is NT$4,685
NT$5,083 total
includes taxes & fees
Oct 27 - Oct 28
Riverside Hotel, an Ascend Collection Hotel
Exterior
The Equinox Golf Resort & Spa
The Equinox Golf Resort & Spa
4.5 star property
7.4 out of 10, Good, (557)
"Beautiful hotel! "
United States
sarah
The price is NT$3,705
NT$5,728 total
includes taxes & fees
Nov 2 - Nov 3
The Equinox Golf Resort & Spa
Indoor spa tub
The Black Bear Lodge at Stratton Mountain Resort
The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
7.6 out of 10, Good, (930)
"Great place for the price "
United States
Karen
The price is NT$4,588
NT$5,551 total
includes taxes & fees
Oct 26 - Oct 27
The Black Bear Lodge at Stratton Mountain Resort
Indoor pool
Pointe at Castle Hill Resort
Pointe at Castle Hill Resort
3.5 star property
8.8 out of 10, Excellent, (907)
"It was a beautiful place "
United States
Tony
The price is NT$4,896
NT$5,581 total
includes taxes & fees
Oct 26 - Oct 27
Pointe at Castle Hill Resort
Interior
The Inn at Weathersfield
The Inn at Weathersfield
4.0 star property
9.8 out of 10, Exceptional, (69)
"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
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0 star property
9.0 out of 10, Wonderful, (763)
"It is Good place to stay. We enjoyed our stay here."
United States
Lokesh
The price is NT$3,972
NT$4,749 total
includes taxes & fees
Nov 24 - Nov 25
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Reception
Courtyard by Marriott Keene Downtown
Courtyard by Marriott Keene Downtown
3.0 star property
8.8 out of 10, Excellent, (1001)
"Lovely hotel"
United States
ronald
The price is NT$5,080
NT$5,512 total
includes taxes & fees
Nov 2 - Nov 3
Courtyard by Marriott Keene Downtown
Hiking
Latchis Hotel
Latchis Hotel
2.5 star property
8.4 out of 10, Very Good, (807)
"Is a great historic building with great charm. Hope to stay there again soon."
United States
Roger
The price is NT$4,295
NT$4,725 total
includes taxes & fees
Nov 3 - Nov 4
Latchis Hotel
Property amenity
The Palmer House Resort, an Ascend Collection Hotel
The Palmer House Resort, an Ascend Collection Hotel
3.0 star property
8.4 out of 10, Very Good, (848)
"Good location; charming property "
United States
Megan
The price is NT$3,900
NT$4,797 total
includes taxes & fees
Nov 2 - Nov 3
The Palmer House Resort, an Ascend Collection Hotel
Front of property
Colonel Williams Inn
Colonel Williams Inn
3.0 star property
9.8 out of 10, Exceptional, (336)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is NT$4,849
NT$5,335 total
includes taxes & fees
Nov 3 - Nov 4
Colonel Williams Inn
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 Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

10/10 Excellent
"Everyone was friendly from front desk to restaurant staff and even the staff painting the elevator. Pablo at the front desk and Emma at the Spa especially stood out."
Vivian 1-night trip
Posted 1 day ago
The Equinox Golf Resort & Spa

Explore a world of travel with Expedia

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.
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.