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Find Romantic Hotels in Woodstock, NY from $117

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Check availability on Woodstock Romantic Hotels

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Dec 6 - Dec 7
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Top Woodstock Romantic Hotels

Children's area
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, (45)
"I was in town for a few days to get some writing done and see friends. The cabin is beautiful and perfect for one or two people and a dog. The location is also perfect; it's in walking distance (or a very short drive) to town, but the main draw is that it's located on a beautiful stream. The rooster crowing in the background and the deer who visited the property were welcome. "
United States
Shannon F.
$279 nightly
The price is $312
Dec 7 - Dec 8
Total with taxes and fees
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Studio, Private Bathroom, Garden View (Dove house on Tannery br) | View from property
Morning Glory B n B Woodstock NY

Morning Glory B n B Woodstock NY

3.0 star property
Woodstock
8.4 out of 10, Very Good, (155)
"Beautiful historic home. We had a nice stay. "
United States
Anonymous traveler
$189 nightly
The price is $212
Dec 7 - Dec 8
Total with taxes and fees
Morning Glory B n B Woodstock NY
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, (261)
"Jane was very nice and accommodating, the cottage was very clean and comfortable, a very relaxing and calming place "
United States
Scott
$346 nightly
The price is $388
Dec 13 - Dec 14
Total with taxes and fees
Streamside Cottage Half Mile to Town of Woodstock
Outdoor pool
Woodstock Historic Artist Estate - The Museum House

Woodstock Historic Artist Estate - The Museum House

Woodstock
10.0 out of 10, Exceptional, (6)
"We had a short stay but absolutely loved the house. Perfect location, lots of space, and the hosts were great. Would stay again, highly recommend!"
United States
Strati P.
$846 nightly
The price is $948
Dec 7 - Dec 8
Total with taxes and fees
Woodstock Historic Artist Estate - The Museum House
Lobby sitting area
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3.0 star property
Hunter
9.2 out of 10, Wonderful, (817)
"Wonderful views, location, and accommodations. I would gladly return to Hunter Lodge"
United States
Russel
$174 nightly
The price is $188
Dec 15 - Dec 16
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
Front of property
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 star property
Rhinebeck
8.4 out of 10, Very Good, (800)
"Really enjoyed staying at this lovely property."
United States
Kenneth
$104 nightly
The price is $117
Jan 1 - Jan 2, 2026
Total with taxes and fees
Beekman Arms and Delamater Inn
Balcony
The Nest Hudson

The Nest Hudson

3.5 star property
Hudson
9.6 out of 10, Exceptional, (209)
"What a beautiful stay right in the heart of Hudson. Cute, cozy, super clean with everything you need! "
United States
Kseniya
$109 nightly
The price is $122
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Nest Hudson
Restaurant
Urban Cowboy Lodge

Urban Cowboy Lodge

5.0 star property
Big Indian
9.2 out of 10, Wonderful, (187)
" Didn’t get the room shown on Expedia website so we were disappointed in that. Overall nice place and really enjoyed our stay. "
United States
Stuart
$144 nightly
The price is $161
Dec 7 - Dec 8
Total with taxes and fees
Urban Cowboy Lodge
Restaurant
Hotel Kinsley

Hotel Kinsley

3.5 star property
Stockade District
9.0 out of 10, Wonderful, (330)
"Room was great and staff very friendly"
Canada
Byron
$256 nightly
The price is $287
Jan 5 - Jan 6, 2026
Total with taxes and fees
Hotel Kinsley
Deluxe Room, 1 King Bed, Balcony | Premium bedding, pillowtop beds, minibar, in-room safe
Diamond Mills Resort

Diamond Mills Resort

3.5 star property
Saugerties
9.4 out of 10, Exceptional, (344)
"Amazing view from the room. We had a great stay. "
United States
Adam
$341 nightly
The price is $379
Dec 7 - Dec 8
Total with taxes and fees
Diamond Mills Resort
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.
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Find out more about Woodstock

Woodstock attractions for couples

Woodstock, New York, is a paradise of artistic and outdoor adventures that will captivate quality-seeking travelers. Start your exploration at the iconic Woodstock Playhouse, where you can catch a live performance in a historic venue that has hosted legendary artists since the 1930s. For art lovers, the Woodstock Artists Association & Museum showcases the rich artistic history of this town, featuring works from local talents and rotating exhibitions that highlight contemporary artists. Outdoor enthusiasts will relish a hike through the stunning Overlook Mountain Trail, which leads to breathtaking views and the remnants of an old hotel, perfect for a family adventure. Don't miss the chance to visit the charming shops and cafés in the heart of town; the local artisan boutiques offer unique crafts and gifts, while the cozy eateries serve up locally sourced dishes that reflect the region's culinary creativity. For a comfortable stay, consider the accommodations around Tinker Street, where boutique hotels and cozy B&Bs provide personalized service and easy access to these attractions, ensuring a seamless blend of relaxation and adventure for your family.

Find the best romantic hotels in Woodstock

For couples seeking a romantic getaway in the picturesque town of Woodstock, New York, these delightful hotels promise an enchanting experience with a blend of charm and comfort.

Twin Gables of Woodstock

  • Why it's great for a couples retreat: Ideal for a romantic retreat, Twin Gables of Woodstock offers a serene atmosphere with a remarkable guest review rating of 9.8. This Victorian gem invites couples to unwind in style, featuring a lovely terrace and beautiful gardens that enhance the intimate ambiance. The hotel serves a complimentary breakfast, ensuring a delightful start to each day of your romantic escape.
  • Other amenities: Additional features include premium bedding for a restful night's sleep, self-parking for added convenience, and nearby hiking and biking trails for adventurous couples. Guests can also indulge in the stunning mountain views that surround the hotel, perfect for those romantic strolls. With daily housekeeping and a cozy atmosphere, this hotel makes for an ideal romantic getaway.
  • Nearby attractions: Catskill State Park - 0.0 miles, SweetHeart Gallery - 0.11 miles, Woodstock Public Library - 0.13 miles

The Herwood Inn

  • Why it's great for a couples retreat: The Herwood Inn is a luxurious escape for couples, offering a romantic atmosphere complemented by a fabulous guest review rating of 9.6. This elegant hotel features an onsite spa and hot tub, perfect for indulging in relaxation together. Guests can also enjoy the beautiful terrace and garden, providing a serene backdrop for intimate moments.
  • Other amenities: Additional amenities include champagne service for special occasions, designer toiletries, and premium bedding to enhance the romantic experience. The inn also provides self-parking and a kitchenette for convenience, ensuring guests have all they need for a comfortable stay. With easy access to outdoor adventures and nearby skiing, The Herwood Inn is perfect for couples looking to blend relaxation with a bit of excitement.
  • Nearby attractions: Catskill State Park - 0.0 miles, SweetHeart Gallery - 0.46 miles, Woodstock Public Library - 0.34 miles

Woodstock Way Hotel

  • Why it's great for a couples retreat: Experience romance at its finest at Woodstock Way Hotel, an impressive guest review rating of 9.4. This upscale hotel features luxurious amenities such as in-room massages and a spa, providing couples with the perfect opportunity to relax and rejuvenate together. The romantic ambiance is enhanced by cozy fireplaces and designer toiletries, ensuring a memorable stay.
  • Other amenities: Couples will appreciate the onsite shopping and the nearby wineries for romantic outings. Other popular amenities include a terrace for enjoying the scenic views, a fully equipped kitchen, and complimentary housekeeping. For those looking to explore, the hotel is conveniently located near concert venues and local attractions, making it a fantastic base for a romantic adventure.
  • Nearby attractions: Catskill State Park - 0.0 miles, SweetHeart Gallery - 0.09 miles, Woodstock Music Shop - 0.16 miles

The Woodstock Inn on the Millstream

  • Why it's great for a couples retreat: The Woodstock Inn on the Millstream is a charming choice for couples searching for a cozy, romantic retreat. With a solid guest review rating of 8.8, this inn offers a tranquil atmosphere complemented by beautiful mountain views. Guests can enjoy a complimentary breakfast, perfect for starting the day in a delightful way, and relax by the fireplace in the evening, adding warmth to their romantic getaway.
  • Other amenities: The inn features a private terrace, air conditioning for comfort, and designer toiletries to enhance the stay. Additional amenities include a fully equipped kitchen, daily housekeeping, and premium bedding, ensuring guests have everything they need for a comfortable and intimate experience.
  • Nearby attractions: Catskill State Park - 0.0 miles, SweetHeart Gallery - 0.23 miles, Woodstock Music Shop - 0.38 miles

Top Woodstock Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Great place for local skiing. Very little local wifi coverage so make sure you have all your check-in details in advance. Nice spot."
Bruce 1-night trip
Posted 6 days ago
Hotel Vienna

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 Woodstock Music Shop, Overlook Mountain Trailhead, 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.
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 Woodstock Music Shop, Overlook Mountain Trailhead, 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.

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