Romantic Hotel in Chester: Find Romantic Hotel in Chester

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

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 Hotel

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Chester romantic hotels

Coffee/tea maker, fridge, microwave, oven

2 bedrooms, iron/ironing board, free WiFi, bed sheets

1. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Eleanor D.

HK$1,333

HK$2,898 total

includes taxes & fees

25 Aug - 26 Aug

Coffee/tea maker, microwave, oven, stovetop

2. 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

Ludlow

Justin P.

HK$1,933

HK$3,958 total

includes taxes & fees

21 Aug - 22 Aug

Shower, eco-friendly toiletries, hair dryer

3. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Walpole

Kelly

HK$2,304

HK$2,857 total

includes taxes & fees

23 Aug - 24 Aug

4. Entire Farmhouse with lots of open space 15 min north of Keene

Walpole

Sean M.

HK$2,818

HK$3,500 total

includes taxes & fees

23 Aug - 24 Aug

5. Family Friendly Hilltop House In Putney Vermont

Putney

Susan O.

HK$1,291

HK$2,412 total

includes taxes & fees

1 Sept - 2 Sept

6. Two Double bed Standard Hotel room 219

Killington

David

HK$640

HK$1,025 total

includes taxes & fees

29 Aug - 30 Aug

7. Deluxe 1 bedroom suite located on first floor with outdoor heated pool 118/120

Killington

Benjamin F.

HK$906

HK$1,340 total

includes taxes & fees

21 Aug - 22 Aug

1 bedroom, iron/ironing board, WiFi, bed sheets

8. Two Queen Bed Standard Hotel room with outdoor heated pool 201

Killington

Lucy Marshall

HK$640

HK$1,027 total

includes taxes & fees

23 Aug - 24 Aug

View all properties

Top Chester Hotel Reviews

The Equinox Golf Resort & Spa

10/10 Excellent

"We loved this hotel, really nice amenities, great rooms. I wish we had planned less activities and spent more time at the hotel. If you want to stay in the hotel, plan to spend a day in the hotel. Breakfast ends at 11 and bar closes at around 10 depending on crowd."

Frequently asked questions

Searching for romantic hotels in Chester?

If you and your partner need a romantic holiday, we'd like to help you plan for it. Our guests also enjoy Chester for its shopping, coffee shops and skiing. If you want to explore the area, you might head to DaVallia Art & Accents or Bonnie's Bundles Dolls. If you'd like to stay close to a certain attraction, you can sort properties by neighbourhood and proximity to top sights, so you'll be able to see everything on your list.

What's the best hotel for couples in Chester?

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO! is a favourite guest house 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, take a look at these details about year-round temperatures in Chester: The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.

What is there to do in Chester?

There's nothing better than seeing 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 coffee shops, restaurants and skiing. You might consider stopping 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 get off to a smooth start: The closest major airport is in Springfield, VT (VSF-Hartness State), located 6.6 mi (10.7 km) from the city centre. If you'd like to explore around the area, consider renting a car to explore more sights.

Explore a world of travel with Expedia

United Rental Cars in Brownsville

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Chester Romantic Hotel

Our top choices for Chester romantic hotels

1. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

2. 2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

3. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

4. Entire Farmhouse with lots of open space 15 min north of Keene

5. Family Friendly Hilltop House In Putney Vermont

6. Two Double bed Standard Hotel room 219

7. Deluxe 1 bedroom suite located on first floor with outdoor heated pool 118/120

8. Two Queen Bed Standard Hotel room with outdoor heated pool 201

9. Queen Studio on the 2nd floor with outdoor heated pool 207

10. Two Double bed Hotel Room with outdoor heated pool 216

Top Chester Hotel Reviews

The Equinox Golf Resort & Spa

Frequently asked questions

Explore a world of travel with Expedia