Find Romantic Hotels in Chester, VT from $147

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Top Chester Romantic Hotels

Reception
Courtyard by Marriott Keene Downtown
Courtyard by Marriott Keene Downtown
3.0 star property
8.8 out of 10, Excellent, (1002)
"Lovely hotel"
ronald
$157 nightly
The price is $170
Nov 2 - Nov 3
Total with taxes and fees
Courtyard by Marriott Keene Downtown
Sundeck
Riverside Hotel, an Ascend Collection Hotel
Riverside Hotel, an Ascend Collection Hotel
2.5 star property
9.6 out of 10, Exceptional, (614)
"Loved my stay"
Christine
$152 nightly
The price is $165
Oct 27 - Oct 28
Total with taxes and fees
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, (551)
"Beautiful hotel! "
sarah
$164 nightly
The price is $181
Nov 10 - Nov 11
Total with taxes and fees
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, (927)
"What a great, cozy place! Definitely would stay here again "
Naomi
$153 nightly
The price is $169
Oct 29 - Oct 30
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
Front of property
Colonel Williams Inn
Colonel Williams Inn
3.0 star property
9.8 out of 10, Exceptional, (334)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
scott
$148 nightly
The price is $163
Nov 3 - Nov 4
Total with taxes and fees
Colonel Williams Inn
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, (760)
"It is Good place to stay. We enjoyed our stay here."
Lokesh
$152 nightly
The price is $165
Nov 17 - Nov 18
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Interior
The Inn at Weathersfield
The Inn at Weathersfield
4.0 star property
9.8 out of 10, Exceptional, (68)
"Comfortable room and tasty dinner. Very well run."
Andrew
$286 nightly
The price is $311
Oct 19 - Oct 20
Total with taxes and fees
The Inn at Weathersfield
Indoor pool
Pointe at Castle Hill Resort
Pointe at Castle Hill Resort
3.5 star property
8.8 out of 10, Excellent, (904)
"It was a beautiful place "
Tony
$136 nightly
The price is $148
Oct 29 - Oct 30
Total with taxes and fees
Pointe at Castle Hill Resort
Hiking
Latchis Hotel
Latchis Hotel
2.5 star property
8.4 out of 10, Very Good, (803)
"Great location in downtown Brattleboro, close to shops and restaurants. Staff are friendly and helpful. "
Joycelyn
$133 nightly
The price is $147
Nov 16 - Nov 17
Total with taxes and fees
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, (841)
"Lovely property convenient to center of town "
Melissa
$142 nightly
The price is $156
Nov 2 - Nov 3
Total with taxes and fees
The Palmer House Resort, an Ascend Collection Hotel
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

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"The place was out slightly out of town so it was quiet. "
georgia 2-night trip
Posted 4 days ago
Pointe at Castle Hill 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 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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