A green agricultural field with rows of crops and greenhouses in the distance under a cloudy sky.

Find Romantic Hotels in Chester, NY from CA $476

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Check availability on Chester Romantic Hotels

Tonight
Oct 16 - Oct 17
Tomorrow
Oct 17 - Oct 18
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Chester romantic hotels

A house with a view of a bridge and mountains.
A two-story house with a stone foundation and a patio with outdoor furniture.
A room with a wooden dresser, a mirror, a red chair, and a patterned rug.
A kitchen with a marble table, white chairs, wooden cabinets, a microwave, a toaster, and a clock on the wall.

1. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
United States
Jasmine
CA $281
CA $476 total
includes taxes & fees
Oct 20 - Oct 21
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
A spacious living room with a large L-shaped sectional sofa, a wooden coffee table, and a large window with curtains.
A round glass table with white chairs on a wooden deck, surrounded by lush greenery and trees.
A bedroom with a large bed, a bedside table with a lamp, a small stool, and a potted plant.
A kitchen with wooden cabinets, a black countertop, and a bar stool.

2. Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
Vernon
United States
Joe C.
CA $224
CA $609 total
includes taxes & fees
Oct 19 - Oct 20
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
Interior
A two-story white house with a front porch, a chimney, and a well-maintained lawn.
A large tree with white blossoms in front of a white building.
A wooden-paneled bedroom with a bed, dresser, and a window with curtains.

3. Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets

Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets
Mountainville
United States
Robert D.
CA $1,626
CA $1,900 total
includes taxes & fees
Oct 19 - Oct 20
Storm King Lodge - Storm King Art Center, West Point, Woodbury Commons Outlets
View all properties

Top Chester Hotel Reviews

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Had a really pleasant time on my overnight trip. Definitely will recommend a longer stay."
Keith 1-night trip
Posted 2 hours ago
Crowne Plaza Suffern - Mahwah by IHG
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"Thanks!"
Michael 1-night trip
Posted 11 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Inn on the Hudson

Inn on the Hudson

10/10 Excellent
"Common balcony was nice but it was a surprise."
joyce 1-night trip
Posted 5 days ago
Inn on the Hudson

Frequently asked questions

Searching for romantic hotels in Chester?
Are you and your partner looking for a romantic vacation? Our guests also enjoy Chester for its restaurants and shopping. If you want to explore the area, you might head to Castle Fun Center, Museum Village, or The Rock Sports Complex. If you're interested in staying close to a certain attraction, you can sort by neighborhood or distance to top landmarks, so you'll be able 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 70°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Chester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What is there to do in Chester?
There's nothing better than seeing a new place with your sweetheart, so consider checking out all that Chester has to offer. If you're hoping to see some of the area's cultural attractions, you'll enjoy Chester for its shopping. A visit to Castle Fun Center, Museum Village, or The Rock Sports Complex might be just the ticket when you're checking out the sights.
What's the best way to get to Chester and around town during my romantic getaway?
This information about transportation options in Chester might help your romantic trip get off to a smooth start: To get to Chester, book a flight to Stewart Intl. Airport (SWF), which is the closest major airport, located 13.5 mi (21.7 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.

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