Find Romantic Hotels in Chester, VT from $163

Check availability on Chester Romantic Hotels

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Tonight
Aug 30 - Aug 31
Tomorrow
Aug 31 - Sep 1
Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14

Top Chester Romantic Hotels

Our top choices for Chester romantic hotels

Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.8 out of 10, Exceptional, (315)
"I enjoyed my stay and found the room more than adequately furnished. Wished the bed could be firmer and they could supply meals other than just breakfast."
$148 nightly
The price is $163
Sep 10 - Sep 11
Total with taxes and fees
Colonel Williams Inn
The Inn at Weathersfield
Interior

The Inn at Weathersfield

4.0 star property
9.8 out of 10, Exceptional, (64)
"Great Inn."
The Inn at Weathersfield
Courtyard by Marriott Keene Downtown
Reception

Courtyard by Marriott Keene Downtown

3.0 star property
8.8 out of 10, Excellent, (1006)
"Spacious, comfortable room in easy waking distance to many restaurants and shopping. Staff is warm and welcoming. "
$189 nightly
The price is $205
Sep 4 - Sep 5
Total with taxes and fees
Courtyard by Marriott Keene Downtown
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (104)
"Great stay"
$301 nightly
The price is $327
Aug 31 - Sep 1
Total with taxes and fees
Chesterfield Inn
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

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

9.4 out of 10, Exceptional, (16)
"Highly recommend clean beautiful stay!"
$225 nightly
The price is $254
Sep 1 - Sep 2
Total with taxes and fees
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Jackson Gore Village
Property entrance

Jackson Gore Village

3.0 star property
8.6 out of 10, Excellent, (754)
"Nice place to stay if tou are visiting Ludlow "
$193 nightly
The price is $213
Sep 30 - Oct 1
Total with taxes and fees
Jackson Gore Village
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (532)
"Relaxing "
$439 nightly
The price is $483
Sep 2 - Sep 3
Total with taxes and fees
Woodstock Inn & Resort
Farm Road Estate
Seasonal outdoor pool

Farm Road Estate

3.0 star property
10.0 out of 10, Exceptional, (70)
"It is a beautiful inn but one of the staff members was a little cold"
$215 nightly
The price is $236
Sep 2 - Sep 3
Total with taxes and fees
Farm Road Estate
Family Friendly Hilltop House In Putney Vermont
Property grounds

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
$305 nightly
The price is $342
Sep 13 - Sep 14
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
Echo Lake Inn
Outdoor pool

Echo Lake Inn

2.5 star property
8.6 out of 10, Excellent, (97)
"Charming place, the food was great, rooms clean, and service was excellent"
$191 nightly
The price is $209
Sep 2 - Sep 3
Total with taxes and fees
Echo Lake 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.

Top Chester Hotel Reviews

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.

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