Find Romantic Hotels in Chester, NY

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Check availability on Chester Romantic Hotels

Tonight
3 Feb - 4 Feb
Tomorrow
4 Feb - 5 Feb
This weekend
6 Feb - 8 Feb
Next weekend
13 Feb - 15 Feb

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
5 Feb - 6 Feb
The Dominion House Bed & Breakfast
Exterior

The Abbey Inn & Spa

The Abbey Inn & Spa
4.0 star property
Peekskill
9.2 out of 10, Wonderful, (239 reviews)
"Friendly staff and a great place to get away and recharge!"
United States
Ariana
The price is AED 1,268
AED 1,618 total
includes taxes & fees
4 Feb - 5 Feb
The Abbey Inn & Spa
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, (1,058 reviews)
"Clean room, helpful staff and good bar/restaurant "
United States
Stephen
The price is AED 373
AED 435 total
includes taxes & fees
22 Feb - 23 Feb
DoubleTree by Hilton Hotel Nanuet
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 AED 492
AED 557 total
includes taxes & fees
10 Feb - 11 Feb
SpringHill Suites by Marriott Fishkill
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, (682 reviews)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
The price is AED 633
AED 812 total
includes taxes & fees
8 Feb - 9 Feb
The Thayer Hotel at West Point
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 AED 367
AED 415 total
includes taxes & fees
11 Feb - 12 Feb
Overlook Lodge at Bear Mountain
Bar (on property)

Courtyard by Marriott Montvale

Courtyard by Marriott Montvale
3.0 star property
Montvale
8.6 out of 10, Excellent, (675 reviews)
"Kate at the front desk was wonderful and other staff I interacted with were friendly. Comfortable bed, clean and quiet room!"
United States
Sarah
The price is AED 493
AED 565 total
includes taxes & fees
8 Feb - 9 Feb
Courtyard by Marriott Montvale
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)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is AED 691
AED 1,118 total
includes taxes & fees
4 Feb - 5 Feb
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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, (50 reviews)
"We havld a good time. The room was comfortable and perfectly located!"
United States
Brandy C.
The price is AED 404
AED 884 total
includes taxes & fees
4 Feb - 5 Feb
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Front of property

The Dutchess Inn and Spa at Beacon

The Dutchess Inn and Spa at Beacon
3.5 star property
Beacon
9.2 out of 10, Wonderful, (171 reviews)
"Great room, great location and super friendly staff. "
United States
Victor
The price is AED 1,028
AED 1,183 total
includes taxes & fees
11 Feb - 12 Feb
The Dutchess Inn and Spa at Beacon
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
"easy check-in/check-out"
Taline 1-night trip
Posted 3 weeks ago
Mountain Creek

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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.