Find Romantic Hotels in Chester, NY

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 ￥34,067
￥38,538 total
includes taxes & fees
Jan 19 - Jan 20
The Dominion House Bed & Breakfast
Indoor pool, open 8:30 AM to 9:30 PM, sun loungers

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1,026 reviews)
"Nice clean hotel with friendly staff. "
United States
michelle
The price is ￥14,695
￥17,101 total
includes taxes & fees
Feb 1 - Feb 2
DoubleTree by Hilton Hotel Nanuet
Restaurant

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 ￥15,086
￥17,065 total
includes taxes & fees
Jan 22 - Jan 23
Overlook Lodge at Bear Mountain
Exterior

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG
3.5 star property
Suffern
8.8 out of 10, Excellent, (1,003 reviews)
"Great staff and clean room. "
United States
Jordon
The price is ￥16,969
￥19,747 total
includes taxes & fees
Jan 30 - Jan 31
Crowne Plaza Suffern - Mahwah by IHG
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (146 reviews)
"Had a great stay at the the Borland House Inn a historical setting in a cute town with wonderful staff and a delicious breakfast"
United States
Deborah
Borland House Inn
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, (681 reviews)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
The price is ￥18,825
￥25,414 total
includes taxes & fees
Jan 18 - Jan 19
The Thayer Hotel at West Point
BBQ/picnic area

SpringHill Suites by Marriott Fishkill

SpringHill Suites by Marriott Fishkill
3.0 star property
Fishkill
9.6 out of 10, Exceptional, (1,000 reviews)
"Excellent stay , felt at home during the holiday, sparkled room, excellent breakfast and amazing warm and welcoming staff "
United States
Esther
The price is ￥18,047
￥20,416 total
includes taxes & fees
Feb 8 - Feb 9
SpringHill Suites by Marriott Fishkill
Courtyard

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (749 reviews)
"Room is clean and spacious, staffs are friendly and professional, highly recommended!"
United States
Rocky
The price is ￥26,094
￥31,378 total
includes taxes & fees
Jan 25 - Jan 26
Home2 Suites by Hilton Middletown
Sophia Suite | Premium bedding, individually decorated, individually furnished

The Factory

The Factory
2.0 star property
Beacon
9.8 out of 10, Exceptional, (72 reviews)
"Gorgeous little Hotel. Would 100% stay there again."
United States
Edward
The price is ￥41,963
￥96,619 total
includes taxes & fees
Jan 22 - Jan 23
The Factory
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 ￥25,455
￥30,068 total
includes taxes & fees
Jan 25 - Jan 26
Residence Inn by Marriott Middletown Goshen
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.
View all properties

Top Chester Hotel Reviews

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

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

10/10 Excellent
"Good stay"
Cindy 1-night trip
Posted 4 days ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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 Goosepond Mountain State Park. 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 Goosepond Mountain State Park 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.