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Check availability on Chester Romantic Hotels

Our top choices for Chester romantic hotels

Superior Double Room, Ensuite (Primrose) | Miscellaneous
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"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 ₹19,507
₹22,068 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Dominion House Bed & Breakfast
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1001)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is ₹8,746
₹9,894 total
includes taxes & fees
1 Jan - 2 Jan 2026
Overlook Lodge at Bear Mountain
Interior
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG
3.5 star property
Suffern
8.8 out of 10, Excellent, (1010)
"Good location"
United States
Glenn
The price is ₹10,013
₹11,653 total
includes taxes & fees
15 Jan - 16 Jan 2026
Crowne Plaza Suffern - Mahwah by IHG
Exterior detail
Borland House Inn

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (144)
"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
Bar (on property)
The Thayer Hotel at West Point

The Thayer Hotel at West Point

The Thayer Hotel at West Point
3.5 star property
West Point
9.0 out of 10, Wonderful, (667)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
The price is ₹12,682
₹16,713 total
includes taxes & fees
18 Dec - 19 Dec
The Thayer Hotel at West Point
Sophia Suite | Premium bedding, individually decorated, individually furnished
The Factory

The Factory

The Factory
2.0 star property
Beacon
9.8 out of 10, Exceptional, (72)
"Gorgeous little Hotel. Would 100% stay there again."
United States
Edward
The price is ₹27,220
₹31,337 total
includes taxes & fees
21 Dec - 22 Dec
The Factory
Reception
Courtyard by Marriott Montvale

Courtyard by Marriott Montvale

Courtyard by Marriott Montvale
3.0 star property
Montvale
8.6 out of 10, Excellent, (651)
"Clean, comfortable space. Friendly staff. "
United States
AMANDA
The price is ₹9,982
₹11,441 total
includes taxes & fees
28 Dec - 29 Dec
Courtyard by Marriott Montvale
Property entrance
Mountain Creek

Mountain Creek

Mountain Creek
3.0 star property
Vernon
8.2 out of 10, Very good, (649)
"Glad i stay very nice hotel"
United States
David
The price is ₹21,458
₹26,084 total
includes taxes & fees
18 Dec - 19 Dec
Mountain Creek
Courtyard
Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (744)
"Overall, it was a good one-night stay. The room was clean and spacious, and parking was convenient. However, the breakfast needs significant improvement; the coffee, eggs, and bacon were all served cold. Additionally, the dining area lacked short tables for children to comfortably sit and eat."
United States
JENNY
The price is ₹13,318
₹16,049 total
includes taxes & fees
23 Dec - 24 Dec
Home2 Suites by Hilton Middletown
BBQ/picnic Area
SpringHill Suites by Marriott Fishkill

SpringHill Suites by Marriott Fishkill

SpringHill Suites by Marriott Fishkill
3.0 star property
Fishkill
9.6 out of 10, Exceptional, (999)
"This was a clean and convenient hotel for visiting the Hudson Valley to see the foliage. We were able to visit beautiful Beacon as well as Storm King Art Center which was about 20 minutes away. We would definitely stay again."
United States
Garvin
The price is ₹10,755
₹12,167 total
includes taxes & fees
28 Dec - 29 Dec
SpringHill Suites by Marriott Fishkill
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

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Nice clean room, very comfortable bed. "
Mordechai 1-night trip
Posted 6 days ago
Crowne Plaza Suffern - Mahwah by IHG

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Frequently asked questions

Searching for romantic hotels in Chester?
Are you and your partner in need of a romantic holiday? 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 near a certain attraction, you can sort by neighbourhood and proximity to top sights, 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, take a look at these details about year-round temperatures in Chester: The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chester are January, February, March and April, with each month seeing an average of 16 cm of snowfall.
What is there to do in Chester?
There's nothing better than experiencing 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?
These transportation options in Chester might help your romantic getaway go off without a hitch: To get to Chester, book a flight to Newburgh, NY (SWF-Stewart Intl.), which is the closest major airport, located 13.5 mi (21.7 km) from the city centre. If you'd like to explore around the area, you may want to rent a car for your trip.