Find Romantic Hotels in Chester, NY

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Check availability on Chester Romantic Hotels

Top Chester Romantic Hotels

Superior Double Room, Ensuite (Primrose) | Miscellaneous
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 AED 790
AED 893 total
includes taxes & fees
24 Nov - 25 Nov
The Dominion House Bed & Breakfast
Restaurant
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1008)
"Parking was very easy, beautiful area, very nice staff"
United States
Elizabeth
The price is AED 380
AED 430 total
includes taxes & fees
30 Nov - 1 Dec
Overlook Lodge at Bear Mountain
Lobby
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4.0 star property
Nanuet
8.8 out of 10, Excellent, (1003)
"Very clean very beautiful very good hospitality would stay again"
United States
Bobby
The price is AED 373
AED 435 total
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Hotel Nanuet
Bar (on property)
The Thayer Hotel at West Point

The Thayer Hotel at West Point

3.5 star property
West Point
9.0 out of 10, Wonderful, (656)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
The price is AED 522
AED 686 total
includes taxes & fees
14 Dec - 15 Dec
The Thayer Hotel at West Point
Exterior detail
Borland House Inn

Borland House Inn

3.0 star property
Montgomery
9.2 out of 10, Wonderful, (143)
"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
Interior
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 star property
Suffern
8.8 out of 10, Excellent, (1014)
"Super clean room. Staff was super amazing. Buffet breakfast was reasonable with wide variety and all around excellent. Beautiful stay!! "
United States
Heather
The price is AED 433
AED 504 total
includes taxes & fees
7 Dec - 8 Dec
Crowne Plaza Suffern - Mahwah by IHG
Courtyard
Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown

3.0 star property
Middletown
9.0 out of 10, Wonderful, (739)
"the room was very clean, friendly staff "
United States
Nyowa
The price is AED 526
AED 634 total
includes taxes & fees
30 Nov - 1 Dec
Home2 Suites by Hilton Middletown
Exterior
DoubleTree by Hilton Mahwah

DoubleTree by Hilton Mahwah

4.0 star property
Mahwah
7.8 out of 10, Good, (921)
"Easy check in."
United States
Nancy
The price is AED 419
AED 480 total
includes taxes & fees
25 Nov - 26 Nov
DoubleTree by Hilton Mahwah
Reception
Courtyard by Marriott Montvale

Courtyard by Marriott Montvale

3.0 star property
Montvale
8.6 out of 10, Excellent, (637)
"Great stay "
United States
Kevin Bruce
The price is AED 493
AED 565 total
includes taxes & fees
23 Nov - 24 Nov
Courtyard by Marriott Montvale
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, (315)
"Room and service were excellent."
United States
Cymantha
The price is AED 624
AED 738 total
includes taxes & fees
7 Dec - 8 Dec
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.
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Top Chester Hotel Reviews

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"A++"
Joel 2-night trip
Posted 2 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 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.