Find Romantic Hotels in Montgomery, NY from $117

Start date: Check-in selected.
To Date
End date: Check-out

Check availability on Montgomery Romantic Hotels

Our top choices for Montgomery romantic hotels

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 10 - Dec 11
Total with taxes and fees
Borland House Inn

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1005)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
$104 nightly
The price is $118
Jan 8 - Jan 9, 2026
Total with taxes and fees
Overlook Lodge at Bear Mountain

Resorts World Catskills Casino

4.5 star property
Monticello
8.6 out of 10, Excellent, (1107)
"It is a great place to stay"
United States
Caonabo
$194 nightly
The price is $216
Dec 10 - Dec 11
Total with taxes and fees
Resorts World Catskills Casino

DoubleTree by Hilton Poughkeepsie Convention Center

4.0 star property
Downtown Poughkeepsie
8.4 out of 10, Very Good, (1004)
"Courteous staff, clean and well outfitted rooms, nice breakfast buffet. "
United States
Kaye
$102 nightly
The price is $119
Dec 14 - Dec 15
Total with taxes and fees
DoubleTree by Hilton Poughkeepsie Convention Center

The Thayer Hotel at West Point

3.5 star property
West Point
9.0 out of 10, Wonderful, (666)
"Location was great & staying at a historic hotel was delightful."
United States
Bobby
$174 nightly
The price is $197
Dec 14 - Dec 15
Total with taxes and fees
The Thayer Hotel at West Point

Holiday Inn Express Poughkeepsie by IHG

2.5 star property
Poughkeepsie
8.6 out of 10, Excellent, (1007)
"Great breakfast, very nice staff, clean room."
United States
Lisa
$101 nightly
The price is $117
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express Poughkeepsie by IHG

The Alder at Resorts World Catskills

2.0 star property
Monticello
8.2 out of 10, Very Good, (202)
"Great place to stay "
United States
Darshan
$134 nightly
The price is $151
Jan 7 - Jan 8, 2026
Total with taxes and fees
The Alder at Resorts World Catskills

The Kartrite Resort & Indoor Waterpark

4.0 star property
Monticello
8.2 out of 10, Very Good, (1851)
"Amazing stayed at the resort, second time here and still planning to come in the future!"
United States
Yeshua
$216 nightly
The price is $244
Dec 11 - Dec 12
Total with taxes and fees
The Kartrite Resort & Indoor Waterpark

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
$143 nightly
The price is $173
Dec 21 - Dec 22
Total with taxes and fees
Home2 Suites by Hilton Middletown

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
$139 nightly
The price is $157
Jan 5 - Jan 6, 2026
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 Montgomery

Montgomery attractions for couples

Montgomery, New York, offers a delightful mix of outdoor activities and local history for travelers seeking quality experiences. Explore the scenic beauty of the Hudson Valley by visiting the nearby Orange County Arboretum, where children can enjoy the vibrant gardens and learn about local flora. For a taste of history, the Montgomery Village Historic District showcases charming 19th-century architecture, perfect for a leisurely stroll with family. Adventure seekers can head to the nearby Stewart State Forest for hiking and picnicking amidst stunning vistas, making it a great spot for a family outing. If you’re looking for a unique shopping experience, the quaint shops in downtown Montgomery offer handcrafted goods and local delicacies. After a day of exploration, consider staying at one of the local inns or boutique hotels that provide attentive guest service and comfortable accommodations. Many of these places are conveniently located, allowing you to easily venture out for more adventures while enjoying a cozy home base.

Find the best romantic hotels in Montgomery

For couples looking to ignite romance in Montgomery, New York, these charming hotels provide an inviting atmosphere and delightful amenities perfect for a romantic getaway.

Borland House Inn

  • Why it's great for a couples retreat: The Borland House Inn is a romantic haven with an impressive review rating of 9.4, perfectly suited for couples seeking intimacy and relaxation. Guests can indulge in the unique Couples Dining experience and enjoy the luxurious onsite spa services, ensuring a pampering retreat for both partners.
  • Other amenities: Additional amenities include charming Victorian hotel design, complimentary full breakfast daily, and a serene garden area for leisurely strolls. Guests can also enjoy the cozy fireplace in their rooms, premium bedding for a restful night, and the convenience of self-parking. The inn’s concierge service is available to assist with any special arrangements, further enhancing the romantic experience.
  • Nearby attractions: Orange County Farmers Museum - 3.15 miles, City Winery Hudson Valley - 0.86 miles, Thomas Bull Memorial Park - 3.42 miles

Buck's Homestead B&B

  • Why it's great for a couples retreat: Buck's Homestead B&B offers a quaint and charming atmosphere perfect for couples, a strong review rating of 9.4. With complimentary continental breakfast included, this charming B&B provides a warm and inviting setting for a romantic escape, complete with a terrace to enjoy the scenic surroundings.
  • Other amenities: Additional features include cozy bathrobes for added comfort, air conditioning for a pleasant stay, and free self-parking. The daily breakfast ensures guests start their day on a delightful note, while the peaceful ambiance of the hotel makes it an ideal spot for couples seeking a memorable getaway.
  • Nearby attractions: Orange County Farmers Museum - 2.77 miles, City Winery Hudson Valley - 1.61 miles, Thomas Bull Memorial Park - 4.52 miles

Holiday Inn Express & Suites Montgomery by IHG

  • Why it's great for a couples retreat: Ideal for travelers seeking a cozy base for their romantic escape, the Holiday Inn Express & Suites boasts a welcoming review rating of 8.8. While it may not have specific romantic amenities, guests can enjoy complimentary breakfast and nearby winery tours that set the stage for a charming day together.
  • Other amenities: Additional features include a 24-hour fitness center for staying active as a couple, free self-parking, and a daily housekeeping service to maintain a comfortable environment. The hotel also offers air conditioning and a microwave, ensuring guests have everything they need at their fingertips for a straightforward stay.
  • Nearby attractions: Orange County Farmers Museum - 2.12 miles, City Winery Hudson Valley - 2.55 miles, Thomas Bull Memorial Park - 4.72 miles

Super 8 by Wyndham Montgomery Maybrook

  • Why it's great for a couples retreat: While the Super 8 by Wyndham Montgomery Maybrook offers a more budget-friendly option with a review rating of 6.0, it can still serve as a practical choice for couples on a romantic getaway. Guests can start their day with a complimentary breakfast and enjoy the casual ambiance of the hotel, which provides a cozy retreat after exploring the area.
  • Other amenities: This hotel features daily housekeeping, free self-parking, and air conditioning for added comfort during their stay. The hotel also offers convenient amenities such as cribs for those traveling with little ones, ensuring guests have everything they need for a smooth experience.
  • Nearby attractions: Orange County Farmers Museum - 2.89 miles, City Winery Hudson Valley - 3.32 miles, Thomas Bull Memorial Park - 3.78 miles

Top Montgomery Hotel Reviews

Frequently asked questions

Searching for romantic hotels in Montgomery?
Are you and your partner looking for a romantic getaway? Our guests also enjoy Montgomery for its restaurants. You might consider checking out some of the nearby sights and attractions such as City Winery Hudson Valley, Orange County Arboretum, or Highland Lakes State Park. If you're interested in staying near a certain attraction, you can sort properties 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 Montgomery?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Montgomery: The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Montgomery are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What is there to do in Montgomery?
There's nothing better than wandering around a new destination with your sweetheart, so consider taking time to discover all that Montgomery has to offer. If you and your partner are interested in sampling the area's cuisine, you'll enjoy Montgomery for its restaurants. You might think about visiting City Winery Hudson Valley, Orange County Arboretum, or Highland Lakes State Park.
What's the best way to get to Montgomery and around town during my romantic getaway?
This information about transportation options in Montgomery might help your romantic trip go off without a hitch: The closest major airport is Stewart Intl. Airport (SWF), located 8 mi (12.9 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.

Explore a world of travel with Expedia