Find Romantic Hotels in Round Top, NY from CA $192

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Check availability on Round Top Romantic Hotels

Our top choices for Round Top romantic hotels

Property grounds

Streamside Cottage Half Mile to Town of Woodstock

Streamside Cottage Half Mile to Town of Woodstock
Woodstock
10.0 out of 10, Exceptional, (279 reviews)
"The view in the snow was absolutely gorgeous and the size of the accommodations was perfect!"
United States
Abigail Y.
The price is CA $245
CA $499 total
includes taxes & fees
Jun 5 - Jun 6
Streamside Cottage Half Mile to Town of Woodstock
Interior

West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind
West Kill
10.0 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Vijay S.
The price is CA $240
CA $632 total
includes taxes & fees
May 15 - May 16
West Kill Barnhouse: Ski, Work & Unwind
Terrace/patio

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
woodstock
9.0 out of 10, Wonderful, (47 reviews)
"A gem just minutes from the heart of Woodstock!"
United States
Susannah H.
The price is CA $247
CA $428 total
includes taxes & fees
May 17 - May 18
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Exterior

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (59 reviews)
"Lovely hosts "
United States
Tyler G.
The price is CA $164
CA $286 total
includes taxes & fees
May 18 - May 19
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Property grounds

QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub

QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub
Hunter
9.8 out of 10, Exceptional, (26 reviews)
"Had the best week at Quinn Hollow. Truly the perfect place to relax after days of skiing. Hope to be back!"
United States
Jacqueline G.
The price is CA $343
CA $761 total
includes taxes & fees
May 20 - May 21
QUINN HOLLOW - Hunter Mountain Ski Cabin, Hot Tub
Exterior

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (44 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
The price is CA $110
CA $192 total
includes taxes & fees
May 17 - May 18
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Terrace/patio

The Lakefront Chalet - Ski, Ride, Golf, Bike, Hike

The Lakefront Chalet - Ski, Ride, Golf, Bike, Hike
Hunter
10.0 out of 10, Exceptional, (111 reviews)
"The stay was fantastic!! It was a wonderful location and was so nice with the lake access. "
United States
Lydia S.
The price is CA $403
CA $1,140 total
includes taxes & fees
May 21 - May 22
The Lakefront Chalet - Ski, Ride, Golf, Bike, Hike
Fridge, microwave, oven, stovetop

Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room

Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
Hunter
9.6 out of 10, Exceptional, (13 reviews)
"⭐️⭐️⭐️⭐️⭐️ The most important part of any stay is having a great host — and we truly did! Our host was incredibly welcoming, responsive, and thoughtful, which made the entire experience so much smoother and more enjoyable. The property itself was cozy, well-maintained, and perfectly located to explore Hunter, NY. We felt right at home from the moment we arrived and left with wonderful memories. Highly recommend this place to anyone visiting the area!"
United States
Taha
The price is CA $438
CA $879 total
includes taxes & fees
May 17 - May 18
Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
Property grounds

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants

Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Maplecrest
10.0 out of 10, Exceptional, (22 reviews)
"Great stay, lovely place, friendly host. Everything was perfect!"
United States
Taylor
The price is CA $492
CA $768 total
includes taxes & fees
May 17 - May 18
Close to skiing in Windham and Hunter, hiking, lakes, 20+restaurants
Exterior

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE

THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
Hunter
10.0 out of 10, Exceptional, (276 reviews)
"Clean and spacious lodge, with fun activities available."
United States
D L.
The price is CA $497
CA $1,273 total
includes taxes & fees
May 17 - May 18
THE LUXURY LODGE - SKI, RIDE, GOLF, BIKE, HIKE
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 Round Top Hotel Reviews

Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

10/10 Excellent
"It is a lovely hotel and the staff was equally pleasant and helpful."
Mary 1-night trip
Posted 5 days ago
Courtyard by Marriott Kingston

Frequently asked questions

Searching for romantic hotels in Round Top?
Are you and your partner looking for a romantic vacation? Our guests also enjoy Round Top for its mountain views. If you want to see some of the sights in Round Top, you might consider checking out Catskill State Park. If you'd like to stay close to a particular destination, you can sort by neighborhood or distance 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 Round Top?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Round Top: The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Round Top are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Round Top?
There's nothing better than seeing a new place with your sweetheart, so consider taking time to discover all that Round Top has to offer. Couples looking to get out in nature will enjoy Round Top for its mountain views. Catskill State Park is one of the local sights that might be worth a stop.
What's the best way to get to Round Top and around town during my romantic getaway?
These transportation options in Round Top might help your romantic trip get off to a smooth start: To get to Round Top, book a flight to Hudson, NY (HCC-Columbia County), which is the closest major airport, located 17 mi (27.3 km) from the city center. If you'd like to explore around the area, you may want a rental car for your journey.

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