Find Romantic Hotels in Chester, VT

  • 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

Tonight
25 Mar - 26 Mar
Tomorrow
26 Mar - 27 Mar
This weekend
27 Mar - 29 Mar
Next weekend
3 Apr - 5 Apr

Our top choices for Chester romantic hotels

Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (168 reviews)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is AED 624
AED 1,321 total
includes taxes & fees
26 Mar - 27 Mar
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
TV, books

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is AED 757
AED 933 total
includes taxes & fees
29 Mar - 30 Mar
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is AED 562
AED 1,041 total
includes taxes & fees
7 Apr - 8 Apr
Family Friendly Hilltop House In Putney Vermont
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Perfect spot for Mount Snow "
United States
Bobby
The price is AED 211
AED 1,143 total
includes taxes & fees
26 Mar - 27 Mar
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

Two Double bed Hotel Room with outdoor heated pool 216

Two Double bed Hotel Room with outdoor heated pool 216
Killington
The price is AED 465
AED 684 total
includes taxes & fees
26 Mar - 27 Mar
Two Double bed Hotel Room with outdoor heated pool 216
Property grounds

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Clock Tower Base Area
9.2 out of 10, Wonderful, (29 reviews)
"Great property, clean and close to the slope"
United States
tiliger01
The price is AED 206
AED 854 total
includes taxes & fees
8 Apr - 9 Apr
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Exterior

Two Double Bed Standard Hotel Room with outdoor heated pool 101

Two Double Bed Standard Hotel Room with outdoor heated pool 101
Killington
8.2 out of 10, Very Good, (17 reviews)
"Loved this lodging. Super fun outdoorsy place. Enjoyed the warm pool and grills and picnic table area. Liked the coffee in mornings in the office. "
United States
Dr Arun
The price is AED 465
AED 685 total
includes taxes & fees
26 Mar - 27 Mar
Two Double Bed Standard Hotel Room with outdoor heated pool 101
Property grounds

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities

Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Stratton
7.4 out of 10, Good, (21 reviews)
"A great weekend. The property was clean and comfortable."
United States
Joan P.
The price is AED 503
AED 1,379 total
includes taxes & fees
7 Apr - 8 Apr
Mountain View Condo with Fast WiFi, Shared Hot Tub, & Resort Amenities
Exterior

Two Double bed Standard Hotel room 218

Two Double bed Standard Hotel room 218
Killington
7.0 out of 10, Good, (2 reviews)
"The room was nice, clean and comfortable, but there was no coffee maker, no refrigerator, no microwave... we couldn't even make hot water in our room, let alone coffee. There wasn't even any coffee available in the lobby/office area in the morning! We had a restful stay, but if you're a morning coffee drinker, make sure you plan ahead for no coffee availability at all!!"
United States
Todd
The price is AED 465
AED 685 total
includes taxes & fees
26 Mar - 27 Mar
Two Double bed Standard Hotel room 218
Exterior

107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool

107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Killington
8.0 out of 10, Very Good, (7 reviews)
"Efficient and affordable option for a short stay."
United States
Marnie O.
The price is AED 465
AED 684 total
includes taxes & fees
29 Mar - 30 Mar
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"We come here many years. It is in a close proximity to the Okemo Ski Resort and all local restaurants, and very reasonably priced, particularly for the area. It has its own pool and jacuzzi, and a full spa vith an open pool and sauna on the premices is a special treat. Bella at the spa reception was a great help and atrue jewel of the facilty."
Vlad 2-night trip
Posted 9 hours ago
Pointe at Castle Hill Resort

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.
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.