A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Chester romantic hotels

Garden

1. Fullerton Inn

Fullerton Inn
2.5 star property
Chester Depot
8.2 out of 10, Very Good, (444 reviews)
"We come to Vermont every year and look forward to our annual stay at The Fullerton!"
United States
Sandra
The price is NT$4,513
NT$4,919 total
includes taxes & fees
Aug 31 - Sep 1
Fullerton Inn
Front of property

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (121 reviews)
"Friendly helpful clean. Bathroom clean. Nice pillows. A/c was super because it was very hot outside. Breakfast was very good"
United States
Kathleen
The price is NT$6,763
NT$7,371 total
includes taxes & fees
Aug 5 - Aug 6
Stone Hearth Inn and Eatery
Exterior

3. Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (871 reviews)
"Clean Room, Convenient Location"
United States
Gerry
The price is NT$5,799
NT$6,379 total
includes taxes & fees
Aug 18 - Aug 19
Best Western Springfield Hotel
Lobby sitting area

4. The Hartness House

The Hartness House
3.0 star property
Springfield
8.2 out of 10, Very Good, (349 reviews)
"Fantastic historic house in downtown Springfield, VT. A wonderful place to spend an evening or the weekend. Close to state parks, great restaurants, and kayaking. Wonderful place for a getaway."
United States
Dan
The price is NT$6,014
NT$6,616 total
includes taxes & fees
Aug 3 - Aug 4
The Hartness House
Sauna, aromatherapy, hot stone massages, deep-tissue massages

5. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (1,000 reviews)
"Great place for the family!"
United States
Stephen
The price is NT$5,471
NT$6,237 total
includes taxes & fees
Aug 23 - Aug 24
Pointe at Castle Hill Resort
Interior

6. The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (80 reviews)
"Great location, service and restaurant "
United States
LUDJANE
The price is NT$6,058
NT$7,794 total
includes taxes & fees
Aug 5 - Aug 6
The Inn at Weathersfield
Porch

7. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (270 reviews)
"Delicious breakfast and great communication throughout! Had a very lovely stay at the Harvest Barn Inn"
Canada
Natalie
The price is NT$5,629
NT$6,136 total
includes taxes & fees
Aug 11 - Aug 12
Harvest Barn Inn
Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave | Premium bedding, in-room safe, iron/ironing board, WiFi (free)

8. Claremont Motor Lodge

Claremont Motor Lodge
2.5 star property
Claremont
8.8 out of 10, Excellent, (547 reviews)
"Nice place to stay"
United States
Shane
The price is NT$3,885
NT$4,215 total
includes taxes & fees
Aug 3 - Aug 4
Claremont Motor Lodge
Interior entrance

9. The Common Man Inn & Restaurant

The Common Man Inn & Restaurant
3.5 star property
Claremont
9.6 out of 10, Exceptional, (408 reviews)
"Beautifully decorated old mill right on the river with great restaurant"
United States
Denis
The price is NT$4,500
NT$4,882 total
includes taxes & fees
Aug 31 - Sep 1
The Common Man Inn & Restaurant
Exterior

10. The Putney Inn

The Putney Inn
2.5 star property
Putney
8.4 out of 10, Very Good, (1,001 reviews)
"For the price it was not bad at all."
United States
Carolina
The price is NT$4,006
NT$4,407 total
includes taxes & fees
Aug 2 - Aug 3
The Putney 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.
View all properties

Top Chester Hotel Reviews

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

8/10 Good
"The room was nice and very clean. The bar and waitstaff were friendly and helpful. The biggest disappointment was the outdoor patio/fire pit area because management said that there was a problem with the gas line (but it's been out for at least a week or two), so it was dark and cold on the patio. They did nothing to help rectify the problem when in fact there were at least 30 people trying to enjoy the outdoors. Many requests were made for management to assist, but nothing. It took the friendly bar staff to come up with a solution. She grabbed lanterns from the inside tables to brighten up the darkness - this made people want to stay longer and enjoy drinks with friends. She made the difference that night! Her name started with a "P" and deserves recognition for making a decision that night."
Lynn 1-night trip
Posted 5 days ago
The Equinox Golf Resort & Spa

Frequently asked questions

Searching for romantic hotels in Chester?
If you and your partner need some romantic time away, we've got just the thing. Our guests also enjoy Chester for its shopping, coffeehouses, and skiing. If you want to explore the area, you might head to DaVallia Art & Accents or Bonnie's Bundles Dolls. If you're interested in staying near a certain attraction, you can sort properties by neighborhood and proximity to top sights, so you and your partner will get to see everything on your list.
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.

Explore a world of travel with Expedia