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

Chester Romantic Hotel

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Check availability on Chester Romantic Hotel

Tonight
20 Aug - 21 Aug
Tomorrow
21 Aug - 22 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Chester romantic hotels

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
HK$1,333
HK$2,898 total
includes taxes & fees
25 Aug - 26 Aug
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

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

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Ludlow
United States
Justin P.
HK$1,933
HK$3,958 total
includes taxes & fees
21 Aug - 22 Aug
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

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
United States
Kelly
HK$2,304
HK$2,857 total
includes taxes & fees
23 Aug - 24 Aug
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

Entire Farmhouse with lots of open space 15 min north of Keene
Walpole
United States
Sean M.
HK$2,818
HK$3,500 total
includes taxes & fees
23 Aug - 24 Aug
Entire Farmhouse with lots of open space 15 min north of Keene

5. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
United States
Susan O.
HK$1,291
HK$2,412 total
includes taxes & fees
1 Sept - 2 Sept
Family Friendly Hilltop House In Putney Vermont

6. Two Double bed Standard Hotel room 219

Two Double bed Standard Hotel room 219
Killington
United States
David
HK$640
HK$1,025 total
includes taxes & fees
29 Aug - 30 Aug
Two Double bed Standard Hotel room 219

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

Deluxe 1 bedroom suite located on first floor with outdoor heated pool 118/120
Killington
United States
Benjamin F.
HK$906
HK$1,340 total
includes taxes & fees
21 Aug - 22 Aug
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

Two Queen Bed Standard Hotel room with outdoor heated pool 201
Killington
United States
Lucy Marshall
HK$640
HK$1,027 total
includes taxes & fees
23 Aug - 24 Aug
Two Queen Bed Standard Hotel room with outdoor heated pool 201

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

Queen Studio on the 2nd floor with outdoor heated pool 207
Killington
United States
Laura D.
HK$640
HK$1,025 total
includes taxes & fees
21 Aug - 22 Aug
Queen Studio on the 2nd floor with outdoor heated pool 207

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

Two Double bed Hotel Room with outdoor heated pool 216
Killington
HK$640
HK$1,025 total
includes taxes & fees
23 Aug - 24 Aug
Two Double bed Hotel Room with outdoor heated pool 216
View all properties

Top Chester Hotel Reviews

The Equinox Golf Resort & Spa

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."
Gabriel 2-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 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.

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