The Best Romantic Hotels in Chester, VT from ￥17,511 in 2026

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Our top choices for Chester romantic hotels

1. Fullerton Inn

Chester Depot

Kirsty

￥21,929

￥23,903 total

includes taxes & fees

Aug 31 - Sep 1

Luxury Room, Mountain View | Blackout drapes, WiFi (free), individually decorated

2. Stone Hearth Inn and Eatery

Chester

Kathleen

￥32,954

￥35,920 total

includes taxes & fees

Aug 12 - Aug 13

Suite, 1 King Bed, Non Smoking, Jetted Tub | Laptop workspace, iron/ironing board, rollaway beds (surcharge)

3. Best Western Springfield Hotel

Springfield

Gerry

￥28,256

￥31,082 total

includes taxes & fees

Aug 17 - Aug 18

Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave | Premium bedding, in-room safe, iron/ironing board, WiFi (free)

4. Claremont Motor Lodge

Claremont

Shane

￥16,139

￥17,511 total

includes taxes & fees

Aug 17 - Aug 18

Mansion Suite (Room 2) | Living area | 32-inch flat-screen TV with digital channels, TV, streaming services

5. The Hartness House

Springfield

Dan

￥28,343

￥31,177 total

includes taxes & fees

Aug 18 - Aug 19

Sauna, aromatherapy, hot stone massages, deep-tissue massages

Suite, 1 King Bed, Sofa Bed & Full Kitchen | Private kitchen | Coffee/tea maker

6. Pointe at Castle Hill Resort

Cavendish

Stephen

￥21,321

￥24,306 total

includes taxes & fees

Aug 11 - Aug 12

Standard Room, 2 Queen Beds, Refrigerator & Microwave | Desk, iron/ironing board, rollaway beds (surcharge), WiFi (free)

7. The Putney Inn

Putney

Robert

￥19,523

￥21,475 total

includes taxes & fees

Aug 11 - Aug 12

King Room with Garden View | Egyptian cotton sheets, premium bedding, memory foam beds, WiFi (free)

8. The Inn at Weathersfield

Perkinsville

LUDJANE

￥29,518

￥37,979 total

includes taxes & fees

Aug 11 - Aug 12

View all properties

Top Chester Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"Perfect"

The Equinox Golf Resort & Spa

8/10 Good

"Good place to stay, but not great."

Kimpton Taconic Hotel by IHG

10/10 Excellent

"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."

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.

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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Change your mind

Treat yourself

Be picky

Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

1. Fullerton Inn

2. Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

4. Claremont Motor Lodge

5. The Hartness House

6. Pointe at Castle Hill Resort

7. The Putney Inn

8. The Inn at Weathersfield

9. Harvest Barn Inn

10. Blue Gentian Lodge at Magic Mountain

Top Chester Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

The Equinox Golf Resort & Spa

Kimpton Taconic Hotel by IHG

Frequently asked questions

Explore a world of travel with Expedia

Find Romantic Hotels in Chester, VT

Change your mind

Treat yourself

Be picky

Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

1. Fullerton Inn

2. Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

4. Claremont Motor Lodge

5. The Hartness House

6. Pointe at Castle Hill Resort

7. The Putney Inn

8. The Inn at Weathersfield

9. Harvest Barn Inn

10. Blue Gentian Lodge at Magic Mountain

Top Chester Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

The Equinox Golf Resort & Spa

Kimpton Taconic Hotel by IHG

Frequently asked questions

Explore a world of travel with Expedia