Find Romantic Hotels in Chester, NY

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Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

Exterior

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233 reviews)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
The price is AED 790
AED 893 total
includes taxes & fees
16 Feb - 17 Feb
The Dominion House Bed & Breakfast
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (150 reviews)
"Breakfast was hot and tasty. Staff were all pleasant and accommodating. "
United States
wendy
Borland House Inn
Reception

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,001 reviews)
"The stone lodges are cute and cozy and the staff were quick and helpful if you needed anything. Great for a short stay at a reasonable price."
United States
Judith
The price is AED 367
AED 415 total
includes taxes & fees
16 Feb - 17 Feb
Overlook Lodge at Bear Mountain
Front of property

Villa Verde BB Greenwood Lake NY

Villa Verde BB Greenwood Lake NY
4.0 star property
Monroe
10.0 out of 10, Exceptional, (16 reviews)
"Excellent stay and delicious breakfast. Clear communication!"
United States
Linda
The price is AED 662
AED 749 total
includes taxes & fees
15 Feb - 16 Feb
Villa Verde BB Greenwood Lake NY
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (131 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is AED 691
AED 1,118 total
includes taxes & fees
15 Feb - 16 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Lobby sitting area

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
West Point
9.0 out of 10, Wonderful, (687 reviews)
"Beautiful architecture, friendly and profesional staff. Great dinning at MacArthur’s Riverview. Convenient and accesible for those visiting USMA."
United States
Sandra M
The price is AED 650
AED 831 total
includes taxes & fees
16 Mar - 17 Mar
The Thayer Hotel at West Point
Exterior detail

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Beacon
10.0 out of 10, Exceptional, (51 reviews)
"We havld a good time. The room was comfortable and perfectly located!"
United States
Brandy C.
The price is AED 422
AED 913 total
includes taxes & fees
19 Feb - 20 Feb
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
View from property

Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (319 reviews)
"Always amazing was my second time here and will stay again."
United States
CiCi
The price is AED 591
AED 699 total
includes taxes & fees
19 Feb - 20 Feb
Residence Inn by Marriott Middletown Goshen
Courtyard

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (750 reviews)
"Room is clean and spacious, staffs are friendly and professional, highly recommended!"
United States
Rocky
The price is AED 537
AED 648 total
includes taxes & fees
15 Feb - 16 Feb
Home2 Suites by Hilton Middletown
Exterior

Mountain Creek

Mountain Creek
3.0 star property
Vernon
8.0 out of 10, Very Good, (687 reviews)
"Great stay and location for skiing. no front desk. the guy on the counter on the store was running the whole show."
United States
ralph
The price is AED 1,071
AED 1,292 total
includes taxes & fees
22 Feb - 23 Feb
Mountain Creek
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

Mountain Creek

Mountain Creek

10/10 Excellent
"Perfect for a solo trip. Room was clean and cozy. They let me park all day in the garage, despite the 11am check out, which is a huge perk. Hot tub is nice, too."
Joshua 1-night trip
Posted 4 days ago
Mountain Creek
HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie

10/10 Excellent
"All was good no complaints "
Alex 1-night trip
Posted 4 days ago
HYATT house Fishkill/Poughkeepsie

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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, The Rock Sports Complex, or Museum Village. 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, The Rock Sports Complex, or Museum Village 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.