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

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Check availability on Chester Romantic Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

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.

1. Pointe at Castle Hill Resort

Pointe at Castle Hill Resort
3.5 star property
Cavendish
8.8 out of 10, Excellent, (1,001 reviews)
"Amazing rooms, sweet staff, great amenities - gorgeous location!"
United States
Cristian
The price is NT$4,662
NT$5,315 total
includes taxes & fees
Nov 1 - Nov 2
Pointe at Castle Hill Resort
A rustic dining area with wooden beams, tables, chairs, and a fireplace.

2. The Inn at Weathersfield

The Inn at Weathersfield
4.0 star property
Perkinsville
9.8 out of 10, Exceptional, (83 reviews)
"Such a nice and kind family of owners. Breakfast was delicious, as well as dinner the previous night in their restaurant. It’s a very rustic Inn, full of history and charm. We would love to return in the near future."
United States
Dorrie
The price is NT$6,708
NT$8,505 total
includes taxes & fees
Nov 29 - Nov 30
The Inn at Weathersfield
A calm lake reflecting a forest with autumn foliage.

3. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (126 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is NT$4,831
NT$5,314 total
includes taxes & fees
Nov 5 - Nov 6
Blue Gentian Lodge at Magic Mountain
A hotel entrance with a wooden porch, a sign reading 'Ascend Collection Hotel,' and potted plants.

4. Sun Lodge near Manchester VT, Ascend Collection Hotel

Sun Lodge near Manchester VT, Ascend Collection Hotel
3.5 star property
Bromley Mountain
8.8 out of 10, Excellent, (354 reviews)
"Great staff, rooms and the best view"
United States
Lynn
The price is NT$3,346
NT$3,680 total
includes taxes & fees
Nov 18 - Nov 19
Sun Lodge near Manchester VT, Ascend Collection Hotel
A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

5. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property
3.0 star property
Jackson Gore Base Area
8.6 out of 10, Excellent, (961 reviews)
"Excellent place to stay!! The breakfas it good, bed comfortables and the view is nice."
United States
Adriana
The price is NT$5,988
NT$7,275 total
includes taxes & fees
Nov 18 - Nov 19
Jackson Gore Village, A Vail Resorts Property
A stone fire pit with chairs around it, set in a grassy area with trees and a large building in the background.

6. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0 star property
Brownsville
9.0 out of 10, Wonderful, (895 reviews)
"Great staff and very good food at the resturant. Will come back in the future!"
United States
Richard
The price is NT$4,502
NT$5,443 total
includes taxes & fees
Nov 1 - Nov 2
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
A white two-story house with a front porch, a covered patio, and a well-maintained garden.

7. The Weston

The Weston
5.0 star property
Weston
10.0 out of 10, Exceptional, (13 reviews)
"The Weston is a spectacular small hotel. The restaurant is delicious and the staff go oabove and beyond to make your stay lovely."
United States
astrid
The price is NT$12,806
NT$13,959 total
includes taxes & fees
Nov 1 - Nov 2
The Weston
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

8. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (63 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is NT$3,466
NT$3,778 total
includes taxes & fees
Nov 2 - Nov 3
Four Columns Inn
A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.

9. Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.2 out of 10, Wonderful, (450 reviews)
"It was a great stay"
United States
Keith
The price is NT$2,788
NT$3,067 total
includes taxes & fees
Nov 16 - Nov 17
Brittany Motel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"Our room was very nice and it’s very peaceful only bad thing pool is down till 2028"
Jennifer 1-night trip
Posted 21 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
On The River Inn

On The River Inn

10/10 Excellent
"Great place would stay again"
Joseph 2-night trip
Posted 4 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 DaVallia Art & Accents or Bonnie's Bundles Dolls. 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.
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 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 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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