Find Romantic Hotels in Chester, VT from CA $178

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Check availability on Chester Romantic Hotels

Tonight
Mar 3 - Mar 4
Tomorrow
Mar 4 - Mar 5
This weekend
Mar 6 - Mar 8
Next weekend
Mar 13 - Mar 15

Our top choices for Chester romantic hotels

Property amenity

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow
2.0 star property
West Dover
8.8 out of 10, Excellent, (65 reviews)
"Clean cozy rooms, overall good stay"
United States
Wade
The price is CA $184
CA $203 total
includes taxes & fees
Mar 24 - Mar 25
Hideaway Inn Mt. Snow
Interior

The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
10.0 out of 10, Exceptional, (74 reviews)
"Everything was really lovely, clean and nice. Loved the downstairs lounge and bar areas, so warm and relaxing. The host was extremely gracious. Looking forward to going back soon! "
United States
James
The price is CA $215
CA $285 total
includes taxes & fees
Mar 8 - Mar 9
The Inn at Weathersfield
Room 4

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (349 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is CA $205
CA $226 total
includes taxes & fees
Mar 9 - Mar 10
Colonel Williams Inn
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, (167 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 CA $232
CA $501 total
includes taxes & fees
Mar 18 - Mar 19
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Interior entrance

The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (378 reviews)
"We loved staying here! It is very quaint, everyone is friendly and the restaurant is great!"
United States
Erica
The price is CA $206
CA $224 total
includes taxes & fees
Mar 24 - Mar 25
The Common Man Inn & Restaurant
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, (999 reviews)
"Friendly staff, clean rooms. "
United States
Kirt
The price is CA $210
CA $240 total
includes taxes & fees
Mar 8 - Mar 9
Pointe at Castle Hill Resort
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 CA $279
CA $343 total
includes taxes & fees
Mar 4 - Mar 5
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior

Latchis Hotel

Latchis Hotel
2.5 star property
Brattleboro
8.4 out of 10, Very good, (851 reviews)
"Great room, friendly & helpful staff, plus a great location in the community"
United States
Jude
The price is CA $161
CA $178 total
includes taxes & fees
Mar 10 - Mar 11
Latchis Hotel
American cuisine

The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
4.0 star property
Manchester Village Historic District
9.8 out of 10, Exceptional, (353 reviews)
"Great room, nice staff."
United States
Gary
The price is CA $231
CA $254 total
includes taxes & fees
Mar 8 - Mar 9
The Reluctant Panther Inn and Restaurant
Exterior

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (290 reviews)
"super cute and clean, felt like home after not living there for 4 years!"
United States
MacLean
The price is CA $225
CA $248 total
includes taxes & fees
Mar 29 - Mar 30
The Inn at Manchester
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 Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Shuttle if very efficient and the wait is never long to get to the slopes and village area. Great area for walks and/or with dogs. Although I was hoping for pancakes or waffles with the continental breakfast but was great nonetheless. Had dinner reservations in the village and the shuttle was the way to go on a super cold night. It’s just what you need to be comfortable. Hot tub and sauna was refreshing. I’d would deff recommend staying there again. "
Cherish Kae 1-night trip
Posted 20 hours ago
The Black Bear Lodge at Stratton Mountain Resort

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 Bonnie's Bundles Dolls or DaVallia Art & Accents 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 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 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.

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