Find Romantic Hotels in Woodstock, NY from $128

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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
9.2 out of 10, Wonderful, (44)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
United States
Paul H.
$277 nightly
The price is $310
Oct 26 - Oct 27
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
8.4 out of 10, Very Good, (155)
"Great owner. Friendly, quaint and ver"
United States
Diane
$219 nightly
The price is $245
Oct 27 - Oct 28
Total with taxes and fees
Morning Glory B n B Woodstock NY
Fridge, microwave, oven, stovetop
Woodstock Historic Artist Estate - The Carriage House
Woodstock Historic Artist Estate - The Carriage House
9.8 out of 10, Exceptional, (44)
"We absolutely love this place! Comfortable and great location! It’s our second time staying there and can’t wait to go back!"
United States
Fran W.
$573 nightly
The price is $642
Oct 26 - Oct 27
Total with taxes and fees
Woodstock Historic Artist Estate - The Carriage House
Outdoor pool
Woodstock Historic Artist Estate - The Museum House
Woodstock Historic Artist Estate - The Museum House
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.
$851 nightly
The price is $953
Oct 27 - Oct 28
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
9.2 out of 10, Wonderful, (787)
"Amazing place for a quality weekend."
United States
Eric
$118 nightly
The price is $128
Nov 11 - Nov 12
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
Front of property
Beekman Arms Hotel
Beekman Arms Hotel
3.5 star property
8.2 out of 10, Very Good, (757)
"Fantastic stay, clean, hugh room with fireplace, can walk throughout the town. Great breakfast!!"
United States
Michele
$143 nightly
The price is $162
Oct 28 - Oct 29
Total with taxes and fees
Beekman Arms Hotel
Breakfast, lunch and dinner served
Stonehill's Farmhouse
Stonehill's Farmhouse
3.5 star property
9.8 out of 10, Exceptional, (42)
"Very cute, clean, friendly and well priced country motel! "
United States
Katya
$212 nightly
The price is $237
Oct 26 - Oct 27
Total with taxes and fees
Stonehill's Farmhouse
Deluxe Room, 1 King Bed, Balcony | Premium bedding, pillowtop beds, minibar, in-room safe
Diamond Mills Resort
Diamond Mills Resort
3.5 star property
9.4 out of 10, Exceptional, (333)
"Wonderful place for calm and relaxation!"
United States
Hadassah
$341 nightly
The price is $379
Oct 27 - Oct 28
Total with taxes and fees
Diamond Mills Resort
Restaurant
Hotel Kinsley
Hotel Kinsley
3.5 star property
9.0 out of 10, Wonderful, (320)
"Excellent location, room, & staff."
United States
Bryan
$256 nightly
The price is $287
Nov 23 - Nov 24
Total with taxes and fees
Hotel Kinsley
Balcony
The Nest Hudson
The Nest Hudson
3.5 star property
9.6 out of 10, Exceptional, (206)
"Minus the slight noise outside of the place due to construction, it was great :)"
Canada
Lindsay
$174 nightly
The price is $195
Nov 3 - Nov 4
Total with taxes and fees
The Nest Hudson
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
"Perfect Romantic Getaway! We had an amazing stay at the Vienna Hotel in Windham — cozy, spotless rooms and a warm, welcoming atmosphere. It’s the perfect romantic escape, close to Hunter Mountain and local restaurants but peaceful and relaxing. Loved the thoughtful touches like the complimentary EV charging station! We’ll definitely be back for another getaway. ❤️"
Naveed 1-night trip
Posted 3 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 Overlook Mountain Trailhead, Catskill State Park, or Woodstock Music Shop. 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 Overlook Mountain Trailhead, Catskill State Park, or Woodstock Music Shop 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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