Black dirt region farm Chester New York

Romantic Hotels & Resorts in Chester from AU$368

  • 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

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, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is AU$475
includes taxes & fees
24 June - 25 June
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, (58 reviews)
"Great location and quiet just like we like it. Unit was very charming."
Canada
Thomas
The price is AU$368
includes taxes & fees
1 July - 2 July
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Exterior

Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #241

Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #241
Vernon
8.4 out of 10, Very good, (10 reviews)
"Great spot if staying at mountain creek! "
United States
Anthony
The price is AU$386
includes taxes & fees
24 June - 25 June
Heated Pool Hot Tubs Sauna Gym Mtn Views Appalachian @ Mtn Creek #241
A heated pool

Luxurious updated 1BR Mtn-Front Condo w/ Deck & Fireplace

Luxurious updated 1BR Mtn-Front Condo w/ Deck & Fireplace
Vernon
10.0 out of 10, Exceptional, (104 reviews)
"Everything was excellent "
United States
James F.
The price is AU$413
includes taxes & fees
24 June - 25 June
Luxurious updated 1BR Mtn-Front Condo w/ Deck & Fireplace
Exterior

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #340

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #340
Vernon
9.8 out of 10, Exceptional, (20 reviews)
"Nice place! "
United States
Jaime B.
The price is AU$432
includes taxes & fees
24 June - 25 June
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #340
Exterior

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #342

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #342
Vernon
10.0 out of 10, Exceptional, (26 reviews)
"All amenities were in good condition, my host was great!"
United States
Alex K.
The price is AU$432
includes taxes & fees
24 June - 25 June
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #342
TV, fireplace, DVD player, stereo

Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax

Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
Vernon
8.6 out of 10, Excellent, (98 reviews)
"Very welcoming and spacious "
United States
Anonymous traveller
The price is AU$605
includes taxes & fees
29 June - 30 June
Luxury 3 Br 2 Bath Condo With Steam Shower Ski Golf Relax
Exterior

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #248

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #248
Vernon
10.0 out of 10, Exceptional, (12 reviews)
"Me, my partner and another couple stayed here for a summer weekend, the accommodations were so cozy, everything provided was great! The kitchen was fully equipped and we had pleasant breakfasts in the mornings, we went for the waterpark right around the corner, and we hope to return for the winter season. We all loved the stay! "
United States
David C.
The price is AU$726
includes taxes & fees
24 June - 25 June
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #248
Pool

Lakefront 2BR Condo Across from Mtn Creek | Black Creek Sanctuary #09-23M

Lakefront 2BR Condo Across from Mtn Creek | Black Creek Sanctuary #09-23M
vernon
10.0 out of 10, Exceptional, (16 reviews)
"Great place to stay, excellent location."
United States
Jacob B.
The price is AU$650
includes taxes & fees
25 June - 26 June
Lakefront 2BR Condo Across from Mtn Creek | Black Creek Sanctuary #09-23M
Exterior

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #312

Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #312
Vernon
9.6 out of 10, Exceptional, (32 reviews)
"Loved our stay. Highly recommend and we’d definitely stay again. "
United States
John R.
The price is AU$725
includes taxes & fees
24 June - 25 June
Heated Pool Hot Tubs Sauna Gym Deck Mtn Front Appalachian @ Mtn Creek #312
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"The room was clean, more than adequate, the surroundings are beautiful, peaceful, and quiet never heard another person for three nights. If you have a car everywhere in the Metropolitan area is easily accessible save yourself the toll on the Cuomo and cross the Bear Mountain Bridge for free."
DOUGLAS 3-night trip
Posted 13 hours ago
Overlook Lodge at Bear Mountain

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 Museum Village. 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 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?
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.

Explore a world of travel with Expedia