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

Find Romantic Hotels in Chester, VT from CA $225

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Check availability on Chester Romantic Hotels

Tonight
Sep 28 - Sep 29
Tomorrow
Sep 29 - Sep 30
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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.
An indoor swimming pool with four chairs and a hot tub.
A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.
A sign for Castle Hill Spa surrounded by lush greenery and a well-maintained lawn.

1. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
Cavendish
United States
Cristian
CA $239
CA $272 total
includes taxes & fees
Oct 18 - Oct 19
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
Rula
CA $316
CA $396 total
includes taxes & fees
Sep 29 - Sep 30
The Inn at Weathersfield
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.
A golf course with rolling hills, trees, and a distant mountain range.
A hot tub with a tiled interior and a window in the background.
A balcony with a stone wall and wooden railing overlooking a grassy area with a building in the background.

3. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
United States
Daniel
CA $234
CA $284 total
includes taxes & fees
Sep 30 - Oct 1
Jackson Gore Village, A Vail Resorts Property
A calm lake reflecting a forest with autumn foliage.
A modern house with a pool, surrounded by lush greenery and mountains in the background.
A hot tub on a covered porch with a view of autumn foliage.
A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

4. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
Londonderry
United States
Abigail
CA $239
CA $263 total
includes taxes & fees
Sep 29 - Sep 30
Blue Gentian Lodge at Magic Mountain
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.

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

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
United States
Eleanor D.
CA $240
CA $516 total
includes taxes & fees
Sep 30 - Oct 1
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
A cozy room with a sofa, armchair, and round table, decorated with leaf-patterned artwork and a lamp.
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.
A dining area with a wooden table and chairs, a window with a view, and a bookshelf with books and decorative items.

6. Sun Lodge near Manchester VT, Ascend Collection Hotel

Sun Lodge near Manchester VT, Ascend Collection Hotel
Bromley Mountain
United States
Mary
CA $205
CA $225 total
includes taxes & fees
Sep 30 - Oct 1
Sun Lodge near Manchester VT, Ascend Collection Hotel
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 white house with a porch, wooden chairs, and umbrellas.

7. The Weston

The Weston
Weston
United States
LISA
CA $559
CA $609 total
includes taxes & fees
Oct 20 - Oct 21
The Weston
A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.
A large, white, two-story house with a steeply pitched roof, a balcony, and a staircase leading to the upper floor.
A stone pathway leading to a porch with a wooden railing, surrounded by lush greenery and a lattice fence.
A kitchen with wooden cabinets, a built-in stove, a microwave, and a sink.

8. Windham Hill Inn

Windham Hill Inn
West Townshend
United States
Nadine
CA $263
CA $286 total
includes taxes & fees
Oct 20 - Oct 21
Windham Hill Inn
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.

9. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Brownsville
United States
Shannon
CA $225
CA $268 total
includes taxes & fees
Oct 26 - Oct 27
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
A rustic lodge with stone walls, a stone fireplace, and outdoor seating.
A spacious kitchen with wooden cabinets, a large island, and pendant lighting.
A wooden double door with a 'Welcome' sign above it, a deer sculpture to the right, and a lantern on the left.
A two-story wooden cabin with a stone foundation, large windows, and a wooden porch.

10. Seesaw's Lodge

Seesaw's Lodge
Peru
United States
Michaela
CA $317
CA $345 total
includes taxes & fees
Sep 29 - Sep 30
Seesaw's Lodge
View all properties

Top Chester Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

8/10 Good
"Fireplace didn’t work. Would love to see the coffee at the “market” be available before 7am."
Ashley 3-night trip
Posted 2 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"all was wonderful and well orchestrated"
Peter 3-night trip
Posted 1 day ago
Kimpton Taconic Hotel by IHG
The Manchester View

The Manchester View

10/10 Excellent
"Great value super clean I will be back"
Sarah 1-night trip
Posted 1 day ago
The Manchester View
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"The Dalmatian behind the front desk"
April 2-night trip
Posted 2 days ago
Pointe at Castle Hill Resort
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

8/10 Good
"Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better."
Nancy 3-night trip
Posted 5 days ago
The Equinox Golf Resort And Spa
On The River Inn

On The River Inn

8/10 Good
"Extremely quaint and love the rooms and balcony… Dining room gorgeous Wish there were Apps on the Tv for streaming… that’s all"
Marcia 2-night trip
Posted 10 days ago
On The River Inn

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 Bonnie's Bundles Dolls or DaVallia Art & Accents. 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 Bonnie's Bundles Dolls or DaVallia Art & Accents 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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