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

Chester Hotel Guide - Romantic Hotels in Chester, Vermont

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Check availability on Chester Romantic Hotels

Tonight
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Chester romantic hotels

Exterior
Interior
Room
Dining

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
€307
includes taxes & fees
7 Sept - 8 Sept
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Living area
Room
Bathroom
Room

2. 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
€305
includes taxes & fees
30 Aug - 31 Aug
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Property grounds
Room
Interior
Living area

3. 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.
€381
includes taxes & fees
30 Aug - 31 Aug
Entire Farmhouse with lots of open space 15 min north of Keene
Property grounds
Living area
Living area
Exterior

4. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
United States
Susan G.
€266
includes taxes & fees
1 Sept - 2 Sept
Family Friendly Hilltop House In Putney Vermont
Exterior
Interior
Property grounds
Room

5. Two Queen Bed Standard Hotel Room w/outdoor heated pool 204

Two Queen Bed Standard Hotel Room w/outdoor heated pool 204
Killington
United States
Joe W.
€116
includes taxes & fees
30 Aug - 31 Aug
Two Queen Bed Standard Hotel Room w/outdoor heated pool 204
Exterior
Interior
Pool
Property grounds

6. Two Double Bed Standard Hotel Room with outdoor heated pool 101

Two Double Bed Standard Hotel Room with outdoor heated pool 101
Killington
United States
Dr Arun
€116
includes taxes & fees
30 Aug - 31 Aug
Two Double Bed Standard Hotel Room with outdoor heated pool 101
Exterior
Living area
Property grounds
Room

7. Deluxe One bedroom Queen Suite with outdoor heated pool 203

Deluxe One bedroom Queen Suite with outdoor heated pool 203
Killington
United States
Pamela T.
€126
includes taxes & fees
30 Aug - 31 Aug
Deluxe One bedroom Queen Suite with outdoor heated pool 203
Exterior
Room
Dining
Private kitchen

8. 107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool

107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Killington
United States
Marnie O.
€116
includes taxes & fees
30 Aug - 31 Aug
107 Deluxe Studio Queen, w/ Sleeper sofa w/ outdoor heated pool
Exterior
Property grounds
Interior
Room

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.
€116
includes taxes & fees
31 Aug - 1 Sept
Queen Studio on the 2nd floor with outdoor heated pool 207
Exterior
Property grounds
Interior
Interior

10. Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209

Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209
Killington
United States
Parker D.
€139
includes taxes & fees
29 Aug - 30 Aug
Deluxe One bedroom Queen Suite on the 2nd floor with outdoor heated pool 209
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Top Chester Hotel Reviews

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Rooms were clean and comfortable ,staff was pleasant. Love the Manchester such a beautiful town."
Christina 2-night trip
Posted 2 hours ago
Kimpton Taconic Hotel by IHG
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good
"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."
Chris 2-night trip
Posted 5 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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 11 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.