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Find Romantic Hotels in Woodstock, NY from $299

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Featured Woodstock Romantic Hotels

Charming Woodstock Hideaway With Seasonal Falls
5/5Exceptional! (61 reviews)
Great place and great stay

"We had a very nice stay. Beautiful property in great location. Highly recommend."…"

Reviewed on Jan 20, 2020

Charming Woodstock Hideaway With Seasonal Falls
Mountain Studio  
Escape NYC Fall🍁
Hikers SEPT/NOV 
near ski 
Sun-Th $specials
The price is $299 per night from Oct 31 to Nov 1
4.9/5Exceptional! (28 reviews)
Amazing experience

"Ike and Carole are wonderful hosts who are extremely helpful. The house was cozy, clean and located on a beautiful setting. Perfect weekend getaway!"…"

Reviewed on Oct 21, 2020

Mountain Studio Escape NYC Fall🍁 Hikers SEPT/NOV near ski Sun-Th $specials
Booking Summer 2020 Mountaintop Cottage/pool Just 3 min From Woodstock Village
4.9/5Exceptional! (10 reviews)
Peaceful cottage just outside of town

"This was an excellent option for staying in Woodstock. Having booked without knowing the town we were delighted that the cottage was a a short drive and situated in a quite area with beautiful views. We particularly enjoyed the visit from deer in the mornings. Ike was incredibly helpful and knows ..."…"

Reviewed on Aug 19, 2019

Booking Summer 2020 Mountaintop Cottage/pool Just 3 min From Woodstock Village
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.

Romantic Spa Hotels

Booking Summer 2020 Mountaintop Cottage/pool Just 3 min From Woodstock Village
4.9/5Exceptional! (10 reviews)
Peaceful cottage just outside of town

"This was an excellent option for staying in Woodstock. Having booked without knowing the town we were delighted that the cottage was a a short drive and situated in a quite area with beautiful views. We particularly enjoyed the visit from deer in the mornings. Ike was incredibly helpful and knows ..."…"

Reviewed on Aug 19, 2019

Booking Summer 2020 Mountaintop Cottage/pool Just 3 min From Woodstock Village
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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.

Romantic Hotels and Accommodations in Woodstock

If you and your partner need some romantic time away, we've got just the ticket. While you're in Woodstock, you'll find lots of things to see and do. If you want to explore the sights and attractions with your partner, you might consider stopping by Woodstock Golf Club, Overlook Mountain Trailhead, or Karma Triyana Dharmachakra Monastery.

Whether you'd like to soak in a spa tub or watch the sunset from your balcony, there are 4 hotels and other accommodations in Woodstock.

Expedia travelers pick these hotels and other accommodations for their romantic atmosphere and amenities:

Booking Summer Mountaintop Cottage/pool Just 3 Minutes From Woodstock Village: This property offers ski area access, free WiFi, and a garden. Our guests appreciate its pool.

Charming Woodstock Hideaway With Seasonal Falls: Cabin featuring a kitchen, a balcony, and a living room. Customers give positive reviews for its comfortable beds.

Hikers Haven Sunset Studio #1 Woodstk FOR 13 Years. Privacy. Pool. Views: With a stay at this apartment, you'll have access to ski area access, free WiFi, and a garden. Expedia travelers speak highly of its pool and prime location.

Dreamcatcher Central - Walk/bike to Tinker St Cozy Cottage w/ Mountain Views: This cottage offers a kitchen, free WiFi, and a garden. Our guests appreciate its comfortable beds and walkable location.

When is the Best Time to Visit Woodstock?

Weather can be a major factor for your holiday, so we've pulled together rainfall and temperature stats to help you plan your vacation:

  • Hottest months: July, August, June, and September, with an average temperature of 83°F
  • Coldest months: January, February, December, and March, with an average temperature of 17°F
  • Driest months: February, January, November, and December, with an average rainfall of 3.19 inches
  • Rainiest months: July, October, June, and May, with an average rainfall of 4.50 inches

Sightseeing in and Around Woodstock

There's nothing better than seeing 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 Woodstock Golf Club, Overlook Mountain Trailhead, or Karma Triyana Dharmachakra Monastery while you're seeing the sights.

Expedia travelers also like Woodstock for its:
  • Forests
  • Riverfront
  • Mountain views
  • Coffee

Getting Around Woodstock

To get to Woodstock, book a flight to Hudson, NY (HCC-Columbia County), which is the closest major airport, located 27.2 mi (43.7 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.

Frequently asked questions

Searching for romantic hotels in Woodstock?
Are you looking for a romantic vacation? Couples enjoy Woodstock for its art scene. If you want to explore the sights and attractions with your partner, you might consider stopping by Woodstock Golf Club, Karma Triyana Dharmachakra Monastery, or Overlook Mountain Trailhead.
What's the best place to stay for a romantic vacation in Woodstock?
Booking Summer 2020 Mountaintop Cottage/pool Just 3 min From Woodstock Village is a favorite cottage for couples, and features private pools and an outdoor pool. Another choice for a stay with your sweetheart is Mountain Studio Escape NYC Fall🍁Hikers SEPT/NOV near ski Sun-Th $specials.
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 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Woodstock are December, January, February, and March, with each month seeing an average of 9 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 Woodstock Golf Club, Karma Triyana Dharmachakra Monastery, or Overlook Mountain Trailhead 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 26.4 mi (42.4 km) from the city center. If you’d like to venture out around the area, consider renting a car to take in more sights.

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