Find Romantic Hotels in Chester, VT

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Check availability on Chester Romantic Hotels

Tonight
6 Aug - 7 Aug
Tomorrow
7 Aug - 8 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Top Chester Romantic Hotels

We don't have any properties that match your exact search

Recommended hotels in Chester

Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (92)
"Sweet place to stay"
The price is AED 740
AED 806 total
includes taxes & fees
12 Aug - 13 Aug
Stone Hearth Inn and Eatery
Fullerton Inn
Garden

Fullerton Inn

2.5 star property
8.2 out of 10, Very Good, (370)
"Everything was Awsome friendly staff"
The price is AED 511
AED 557 total
includes taxes & fees
1 Sep - 2 Sep
Fullerton Inn
Historic 150-year-old farmhouse, Jacuzzi included
Exterior

Historic 150-year-old farmhouse, Jacuzzi included

10.0 out of 10, Exceptional, (6)
"This was a lovely inviting piece of history to stay in! The amenities were wonderful, the host very engaged with being sure we had what we needed. It is (for those who may not know Vermont) SUPER close to all sorts of hiking, tours, cute stores and great food! Our family will absolutely stay here again!"
The price is AED 628
AED 1,728 total
includes taxes & fees
7 Aug - 8 Aug
Historic 150-year-old farmhouse, Jacuzzi included
Room in Historic Inn! 20 Minutes to Okemo!
Terrace/patio

Room in Historic Inn! 20 Minutes to Okemo!

9.2 out of 10, Wonderful, (16)
"My stay was brief but was pleased to arrive to beautiful building and a room that was huge, well decorated/furnished, well heated, and super cozy. I would definitely stay here again."
The price is AED 327
AED 572 total
includes taxes & fees
24 Aug - 25 Aug
Room in Historic Inn! 20 Minutes to Okemo!
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Dining

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

8.0 out of 10, Very Good, (1)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
The price is AED 474
AED 769 total
includes taxes & fees
10 Aug - 11 Aug
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Whimsical Room & Private Bathroom in Historic Inn
Interior

Whimsical Room & Private Bathroom in Historic Inn

8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
The price is AED 327
AED 572 total
includes taxes & fees
1 Sep - 2 Sep
Whimsical Room & Private Bathroom in Historic Inn
WhiSki Cabin - 12 Acres With a Mountain View!
Fridge, microwave, oven, stovetop

WhiSki Cabin - 12 Acres With a Mountain View!

10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
The price is AED 1,980
AED 3,612 total
includes taxes & fees
19 Aug - 20 Aug
WhiSki Cabin - 12 Acres With a Mountain View!
Charming Chester Farmhouse – peaceful and close to everything!
Terrace/patio

Charming Chester Farmhouse – peaceful and close to everything!

9.6 out of 10, Exceptional, (12)
"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "
The price is AED 768
AED 1,559 total
includes taxes & fees
7 Aug - 8 Aug
Charming Chester Farmhouse – peaceful and close to everything!
King & Queen Suite in Historic Inn Circa 1780
Interior

King & Queen Suite in Historic Inn Circa 1780

9.6 out of 10, Exceptional, (15)
"The check in process was easy, and the space was beautiful. Great location for a weekend of skiing!"
The price is AED 511
AED 831 total
includes taxes & fees
10 Aug - 11 Aug
King & Queen Suite in Historic Inn Circa 1780
Honeymoon Suite with Jacuzzi Tub in Historic Inn
1 bedroom, desk, iron/ironing board, free WiFi

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"Charming place, hope to go back soon."
The price is AED 364
AED 613 total
includes taxes & fees
1 Sep - 2 Sep
Honeymoon Suite with Jacuzzi Tub in Historic 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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Everything was very well taken care of except the pool building which was an awful first impression of the property since it is the first thing you see upon arrival. Rotten and decaying siding and what isn’t is In need of repainting. A sharp contrast to the rest of the buildings and grounds which were beautiful."
Chris 2-night trip
Posted 5 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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 fitness center.
How many romantic hotels will we find in Chester?
Expedia has 5 romantic Chester hotels for you both to enjoy.
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.