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
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Chester romantic hotels

A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.
A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.
A spacious lobby with a fireplace, leather seating, and a chandelier.
An indoor swimming pool with four chairs and a hot tub.

1. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Cristian
€146
includes taxes & fees
18 Oct - 19 Oct
Pointe at Castle Hill Resort
A rustic dining area with wooden beams, tables, chairs, and a fireplace.
A bedroom with a large bed, a bedside table, a lamp, and a view of the outdoors through a sliding door.
An outdoor event space with tables set for dining, surrounded by a covered area with a transparent roof.
A living room with a sofa, ottoman, armchair, and a television on a stand.

2. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Dorrie
€253
includes taxes & fees
5 Nov - 6 Nov
The Inn at Weathersfield
A calm lake reflecting a forest with autumn foliage.
A house with a balcony and a garden with red flowers.
A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.
A hot tub on a covered porch with a view of autumn foliage.

3. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
United States
Abigail
€146
includes taxes & fees
3 Nov - 4 Nov
Blue Gentian Lodge at Magic Mountain
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.
A hot tub with a tiled interior and a window in the background.
A golf course with rolling hills, trees, and a distant mountain range.
A hotel with a swimming pool area, including two hot tubs and lounge chairs.

4. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Jessica
€200
includes taxes & fees
9 Nov - 10 Nov
Jackson Gore Village, A Vail Resorts Property
A cozy room with a sofa, armchair, and round table, decorated with leaf-patterned artwork and a lamp.
A dining area with a wooden table and chairs, a window with a view, and a bookshelf with books and decorative items.
A bar area with wooden ceiling, shelves with bottles, and a bar counter.
A hotel room with a bed, a chair, a table, and a view of mountains through a large window.

5. Sun Lodge near Manchester VT, Ascend Collection Hotel

Sun Lodge near Manchester VT, Ascend Collection Hotel
Bromley Mountain
United States
Lynn
€117
includes taxes & fees
1 Nov - 2 Nov
Sun Lodge near Manchester VT, Ascend Collection Hotel
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.
A living room with leather sofas, a round ottoman, a fireplace, and a bookshelf.
A long wooden table with red placemats and multiple wine glasses arranged for a tasting.
A serene pond with a statue in the center, surrounded by lush greenery and trees.

6. Four Columns Inn

Four Columns Inn
Newfane
United States
cindy
€104
includes taxes & fees
2 Nov - 3 Nov
Four Columns Inn
A white two-story house with a front porch, a covered patio, and a well-maintained garden.
A bathroom with a glass shelf holding toiletries, a vase with sunflowers, and a window with blinds.
A dining table with plates of food, two glasses of white wine, and a bottle of wine.
A living room with a sofa, a coffee table, and a painting on the wall.

7. The Weston

The Weston
Weston
United States
LISA
€384
includes taxes & fees
20 Oct - 21 Oct
The Weston
A multi-story hotel with a central courtyard and a reflective water feature.
A bar area with stools, a counter, and a large window offering a view of a snowy landscape.
A living room with a fireplace, a sofa, a coffee table, and a television.
A spacious living area with a staircase, patterned sofas, a coffee table, and a decorative wall piece.

8. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Shannon
€150
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.
A living room with a sofa, a coffee table, a chess table, a TV, and a gaming console.
A building with a covered outdoor area, wooden benches, and potted plants.
A cozy room with a sofa, a bed, a wooden table, and a coffee machine.

9. Brittany Motel

Brittany Motel
Manchester Center
United States
Karen B
€84
includes taxes & fees
19 Oct - 20 Oct
Brittany Motel
A red house with a covered porch and a chimney.
A kitchen with white cabinets, a microwave, a stove, and a sink.
A kitchen with a wooden table and chairs, a microwave, and cabinets.
Two single beds with wooden frames and striped bedding, a small wooden nightstand with a lamp, and a window with a view of greenery.

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
€331
includes taxes & fees
12 Oct - 13 Oct
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
View all properties

Top Chester Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

8/10 Good
"Room was adequate. Bedding was uncomfortable. We would not revisit this property. We would not recommend to others."
Bruce 4-night trip
Posted less than an hour ago
Pointe at Castle Hill Resort
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

8/10 Good
"Nice clean rooms comfortable, breakfast was a nice way to start today."
Alain 2-night trip
Posted less than an hour ago
The Black Bear Lodge at Stratton Mountain Resort
The Manchester View

The Manchester View

10/10 Excellent
"We loved this property, our view opened up to magnificent Mountain View, if you are there during lead peeping season you know that makes a difference. We enjoyed the hot tub at night and the fireplace . Kind staff, they left cookies and bowls for our dog, breakfast was delicious, the variety of baked goods was perfect and the Vermont coffee provided brought up to a higher level I can’t wait to go back for a longer stay"
Cathya 1-night trip
Posted 2 days ago
The Manchester View
On The River Inn

On The River Inn

10/10 Excellent
"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."
VS 4-night trip
Posted 5 days ago
On The River Inn
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Beautiful location. Helpful staff"
Richard 1-night trip
Posted 12 days ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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.