Romantic Hotels in Chester, New York

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Check availability on Chester Romantic Hotels

Top Chester Romantic Hotels

The Dominion House Bed & Breakfast
Stroll through the serene garden, surrounded by lush plants and a soothing fountain, with a charming gazebo in the distance.

The Dominion House Bed & Breakfast

2.0 star property
9.2 out of 10, Wonderful, (224)
"The proprietors are lovely, the facilities are beautiful, and the food was delicious. We enjoyed our time here and will definitely return! "
The price is P12,139
P13,732 total
includes taxes & fees
Jul 14 - Jul 15
The Dominion House Bed & Breakfast
The Abbey Inn & Spa
Stroll through the beautifully landscaped grounds, surrounded by flowering plants and large rocks, leading to a building with a unique tower.

The Abbey Inn & Spa

4.0 star property
9.2 out of 10, Wonderful, (185)
"Thanks for a great stay!!"
The Abbey Inn & Spa
SpringHill Suites by Marriott Fishkill
Relax by the fire pit in our outdoor patio area, surrounded by comfortable seating and natural light.

SpringHill Suites by Marriott Fishkill

3.0 star property
9.6 out of 10, Exceptional, (962)
"Excellent stay."
The price is P9,264
P10,480 total
includes taxes & fees
Jul 20 - Jul 21
SpringHill Suites by Marriott Fishkill
The Thayer Hotel at West Point
Relax with a drink at our outdoor bar, featuring a brick counter and stools under a shaded canopy.

The Thayer Hotel at West Point

3.5 star property
9.0 out of 10, Wonderful, (572)
"Good breakfast Beautiful hotel "
The Thayer Hotel at West Point
The Dutchess Inn and Spa at Beacon
Stunning exterior of The Inn and Spa at Beacon, featuring a black metal frame and gold lettering.

The Dutchess Inn and Spa at Beacon

3.5 star property
9.2 out of 10, Wonderful, (165)
"This is a beautiful property in a great location. It was perfect for our couple's getaway. We were able to relax and enjoy our time together. "
The price is P16,997
P19,567 total
includes taxes & fees
Aug 6 - Aug 7
The Dutchess Inn and Spa at Beacon
The Factory
Relax in a spacious room with a large bed, sleek sofa, and separate seating area.

The Factory

2.0 star property
9.8 out of 10, Exceptional, (54)
"Clean and comfortable and good location"
The price is P14,122
P16,257 total
includes taxes & fees
Aug 6 - Aug 7
The Factory
Crowne Plaza Suffern - Mahwah by IHG
Relax in the serene atrium, surrounded by lush greenery and a central water feature.

Crowne Plaza Suffern - Mahwah by IHG

3.5 star property
8.8 out of 10, Excellent, (1011)
"Great place to stay"
The price is P4,849
P5,643 total
includes taxes & fees
Jul 27 - Jul 28
Crowne Plaza Suffern - Mahwah by IHG
Cromwell Manor Inn
Stately two-story house with a central entrance and columns, surrounded by a well-manicured lawn.

Cromwell Manor Inn

3.5 star property
9.4 out of 10, Exceptional, (65)
"Couple who ran the place were amazing, friendly, helpful and adorable Made our stay there wonderful. Really loved everything."
The price is P12,784
P15,101 total
includes taxes & fees
Jul 13 - Jul 14
Cromwell Manor Inn
DoubleTree by Hilton Mahwah
Hotel entrance with a prominent double doorway and symmetrical facade.

DoubleTree by Hilton Mahwah

4.0 star property
7.8 out of 10, Good, (856)
"Had a great stay "
The price is P6,674
P7,650 total
includes taxes & fees
Aug 4 - Aug 5
DoubleTree by Hilton Mahwah
Home2 Suites by Hilton Middletown
Relax by the fire pit surrounded by comfortable seating under a shaded area amidst lush greenery.

Home2 Suites by Hilton Middletown

3.0 star property
9.0 out of 10, Wonderful, (699)
"Been here twice and very family friendly "
The price is P8,510
P10,250 total
includes taxes & fees
Aug 10 - Aug 11
Home2 Suites by Hilton Middletown
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.

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.
What's the best accommodation for a romantic getaway to Chester?
The Dominion House Bed & Breakfast is a favorite 3.5-star B&B for couples, and features wedding services and free breakfast.
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.