Find Romantic Hotels in Woodstock, NY

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Check availability on Woodstock Romantic Hotels

Tonight
Jul 21 - Jul 22
Tomorrow
Jul 22 - Jul 23
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Top Woodstock Romantic Hotels

CHARMING LARGE STUDIO WITH POOL AND MOUNTAIN VIEWS ON 10 ACRES. Close to town
Relax by the pool surrounded by lush greenery and comfortable lounge chairs.

CHARMING LARGE STUDIO WITH POOL AND MOUNTAIN VIEWS ON 10 ACRES. Close to town

10.0 out of 10, Exceptional, (64)
"This is our second time staying here with our 2 year old daughter. The location is great, short drive to main street."
CHARMING LARGE STUDIO WITH POOL AND MOUNTAIN VIEWS ON 10 ACRES. Close to town
Cozy 2 bedroom cottage in Woodstock heated pool, mountain views,bbq,swim 🏊‍♂️ hike
Cozy log cabin-style house with a gabled roof and a welcoming front porch, set amidst a lush lawn and dense forest surroundings.

Cozy 2 bedroom cottage in Woodstock heated pool, mountain views,bbq,swim 🏊‍♂️ hike

9.8 out of 10, Exceptional, (38)
"A great location in Woodstock. Ike was always very helpful and communicative. Had a great time, the cottage decoration and furnishings were beautiful "
Cozy 2 bedroom cottage in Woodstock heated pool, mountain views,bbq,swim 🏊‍♂️ 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.

Frequently asked questions

Searching for romantic hotels in Woodstock?
Are you and your partner looking for a romantic getaway? Our guests also enjoy Woodstock for its art scene. If you want to explore the area, you might head to Overlook Mountain Trailhead, Karma Triyana Dharmachakra Monastery, or Catskill State Park. If you're interested in staying near a certain attraction, you can sort by neighborhood or distance to top sights, so you'll be able to see everything on your list.
What's the best place to stay for a romantic vacation in Woodstock?
This Sioux Tipi is no longer available, but we have one nearby in another town! is a favorite lodge for couples, and features in-room fireplaces and kitchens.
How many romantic hotels are there in Woodstock?
Expedia has 23 romantic Woodstock hotels for you to get cozy in.
When is the best time of year for a romantic getaway to Woodstock?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Woodstock: The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Woodstock are January, February, March, and April, with each month seeing an average of 7 inches of snowfall.
What is there to do in Woodstock?
There's nothing better than experiencing a new place with your sweetheart, so consider checking out all that Woodstock has to offer. If you're hoping to see some of the area's cultural attractions, you'll enjoy Woodstock for its art scene. You might think about stopping by Overlook Mountain Trailhead, Karma Triyana Dharmachakra Monastery, or Catskill State Park while you're seeing the sights.
What's the best way to get to Woodstock and around town during my romantic getaway?
This information about transportation options in Woodstock might help your romantic trip get off to a smooth start: The closest major airport is Hudson, NY (HCC-Columbia County), located 27.2 mi (43.7 km) from the city center. If you'd like to venture out around the area, consider renting a car to take in more sights.