Find Romantic Hotels in Chester, NY from $114

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Top Chester Romantic Hotels

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
$215 nightly
The price is $243
Dec 8 - Dec 9
Total with taxes and fees
The Dominion House Bed & Breakfast

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1002)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
$100 nightly
The price is $114
Dec 16 - Dec 17
Total with taxes and fees
Overlook Lodge at Bear Mountain

DoubleTree by Hilton Hotel Nanuet

4.0 star property
Nanuet
8.8 out of 10, Excellent, (1018)
"Very clean very beautiful very good hospitality would stay again"
United States
Bobby
$98 nightly
The price is $114
Jan 4 - Jan 5, 2026
Total with taxes and fees
DoubleTree by Hilton Hotel Nanuet

Crowne Plaza Suffern - Mahwah by IHG

3.5 star property
Suffern
8.8 out of 10, Excellent, (1001)
"The staff, the cleanliness of the room, the food and overall it was a good stay. Will stay again."
United States
Cynthia
$103 nightly
The price is $120
Jan 1 - Jan 2, 2026
Total with taxes and fees
Crowne Plaza Suffern - Mahwah by IHG

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
$114 nightly
The price is $129
Dec 7 - Dec 8
Total with taxes and fees
Borland House Inn

The Thayer Hotel at West Point

3.5 star property
West Point
9.0 out of 10, Wonderful, (663)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
$176 nightly
The price is $200
Dec 14 - Dec 15
Total with taxes and fees
The Thayer Hotel at West Point

Courtyard by Marriott Montvale

3.0 star property
Montvale
8.6 out of 10, Excellent, (644)
"Great stay "
United States
Kevin Bruce
$116 nightly
The price is $133
Dec 21 - Dec 22
Total with taxes and fees
Courtyard by Marriott Montvale

Home2 Suites by Hilton Middletown

3.0 star property
Middletown
9.0 out of 10, Wonderful, (742)
"the room was very clean, friendly staff "
United States
Nyowa
$143 nightly
The price is $173
Dec 21 - Dec 22
Total with taxes and fees
Home2 Suites by Hilton Middletown

Residence Inn by Marriott Middletown Goshen

3.0 star property
Middletown
9.4 out of 10, Exceptional, (317)
"Room and service were excellent."
United States
Cymantha
$170 nightly
The price is $201
Dec 21 - Dec 22
Total with taxes and fees
Residence Inn by Marriott Middletown Goshen

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
$144 nightly
The price is $163
Dec 7 - Dec 8
Total with taxes and fees
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.

Find out more about Chester

Chester attractions for couples

Chester, New York, a charming town nestled in the picturesque Hudson Valley, offers a delightful mix of outdoor adventures and local charm that will captivate any quality-seeking traveler. Start your exploration at the enchanting Chester Town Park, where you can enjoy spacious picnic areas, a playground for the kids, and scenic walking trails that wind around beautiful ponds. For a taste of local culture, visit the Chester Historical Society, where fascinating exhibits outline the town’s rich history, including its role in the Revolutionary War. Adventurous families will love hiking the nearby trails of the Catskill Mountains, providing breathtaking views and opportunities for wildlife spotting. Don’t miss the chance to sample artisanal products at local farms, such as the renowned Stonewall Farm, where you can pick fresh produce and indulge in homemade treats. For a comfortable stay, consider accommodations within the charming downtown area, where boutique hotels offer modern amenities while retaining a cozy, intimate atmosphere. You’ll be perfectly positioned to explore local eateries and shops, allowing for a seamless blend of relaxation and adventure, ensuring that your family feels pampered and taken care of throughout your visit.

Find the best romantic hotels in Chester

For couples seeking a romantic getaway in Chester, New York, these charming hotels provide the perfect ambiance and amenities for a memorable stay.

The Dominion House Bed & Breakfast

  • Why it's great for a couples retreat: The Dominion House Bed & Breakfast is a top-rated romantic escape, a perfect review rating of 10.0. This intimate setting features charming rooms complete with fireplaces that create a warm and inviting atmosphere, perfect for couples looking to enjoy quality time together.
  • Other amenities: Guests can savor a complimentary breakfast and take advantage of the outdoor pool during warmer months. The hotel offers a delightful terrace and garden space, ideal for leisurely afternoons. Additional features include kitchenettes in the rooms, a billiards table for casual fun, and nearby hiking and biking trails, allowing couples to explore the beautiful surroundings together.
  • Nearby attractions: Brotherhood Winery - 3.09 miles, Schunnemunk State Park - 5.03 miles, Goosepond Mountain State Park - 5.71 miles

Holiday Inn Express Hotel & Suites Chester by IHG

  • Why it's great for a couples retreat: The Holiday Inn Express Hotel & Suites Chester offers a cozy retreat for couples, with an excellent review rating of 8.6. Although it may not have overtly romantic amenities, guests can enjoy a relaxing indoor pool and comfortable accommodations that foster a peaceful environment for couples to unwind together.
  • Other amenities: Guests can indulge in a complimentary breakfast each morning, ensuring a delightful start to the day. The hotel features self-parking, daily housekeeping, and free internet access. The inviting sofa beds in the rooms provide extra comfort, while the nearby local shopping districts offers opportunities for leisurely strolls and shared experiences for couples.
  • Nearby attractions: Castle Fun Center - 0.48 miles, The Rock Sports Complex - 1.48 miles, Museum Village - 1.67 miles

Top Chester Hotel Reviews

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.

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