Woodstock Hotel Guide - Romantic Hotels in Woodstock, New York

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Check availability on Woodstock Romantic Hotels

Top Woodstock Romantic Hotels

Urban Cowboy Lodge
Restaurant

Urban Cowboy Lodge

5.0 star property
9.2 out of 10, Wonderful, (160)
"Amazing! Did not want to leave. Such a cool place to visit. My only complaint is not staying another night. "
The price is €162
includes taxes & fees
18 Aug - 19 Aug
Urban Cowboy Lodge
Stonehill's Farmhouse
Breakfast, lunch and dinner served

Stonehill's Farmhouse

3.5 star property
9.8 out of 10, Exceptional, (32)
"a lovely experience we are planning a return trip when we can stay for more than one night"
The price is €186
includes taxes & fees
17 Aug - 18 Aug
Stonehill's Farmhouse
The Nest Hudson
Balcony

The Nest Hudson

3.5 star property
9.6 out of 10, Exceptional, (200)
"The Nest Hudson is a gem with great amenities and very comfortable bedding. We are riding our bicycles up the state and over to Buffalo, and this place was an oasis that helped us recharge and prep for the next leg of our journey. Food tips: Feast and Floret for an excellent meal and WYLDE Hudson for a morning cafe, both within a short walk. "
The Nest Hudson
Morning Glory B n B Woodstock NY
Studio, Private Bathroom, Garden View (Dove house on Tannery br) | View from property

Morning Glory B n B Woodstock NY

3.0 star property
8.6 out of 10, Excellent, (144)
"We absolutely loved our stay - the white room was clean and lovely. We love the location too - great proximity to Station, movie theater and restaurants."
The price is €190
includes taxes & fees
15 Sept - 16 Sept
Morning Glory B n B Woodstock NY
Streamside Cottage Half Mile to Town of Woodstock
Property grounds

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (248)
"A beautiful quiet setting! "
The price is €297
includes taxes & fees
2 Sept - 3 Sept
Streamside Cottage Half Mile to Town of Woodstock
Woodstock historic artist estate - The Pond House
Exterior

Woodstock historic artist estate - The Pond House

10.0 out of 10, Exceptional, (10)
"Beautiful and relaxing home, very open. It’s like being outside, inside. Lots of nature to explore on the property too. "
The price is €879
includes taxes & fees
18 Aug - 19 Aug
Woodstock historic artist estate - The Pond House
Woodstock Historic Artist Estate - The Museum House
Outdoor pool

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!"
The price is €1,251
includes taxes & fees
19 Aug - 20 Aug
Woodstock Historic Artist Estate - The Museum House
Woodstock Historic Artist Estate - The Carriage House
Fridge, microwave, oven, stovetop

Woodstock Historic Artist Estate - The Carriage House

9.8 out of 10, Exceptional, (41)
"We absolutely love this place! Comfortable and great location! It’s our second time staying there and can’t wait to go back!"
The price is €653
includes taxes & fees
23 Aug - 24 Aug
Woodstock Historic Artist Estate - The Carriage House
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Banquet hall

Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!

9.8 out of 10, Exceptional, (116)
"The location was exceptional, close to restaurants and shops, quiet neighborhood, comfortable bed and the house was well stocked with everything you’d need."
The price is €634
includes taxes & fees
23 Aug - 24 Aug
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Winwood Condominiums by Windham Mountain Club
Seasonal outdoor pool

Winwood Condominiums by Windham Mountain Club

3.0 star property
8.6 out of 10, Excellent, (329)
"Wonderful property "
The price is €184
includes taxes & fees
18 Aug - 19 Aug
Winwood Condominiums by Windham Mountain Club
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.

Top Woodstock Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Great hotel"
Elena 1-night trip
Posted 4 days ago
Hotel Vienna
Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

10/10 Excellent
"Nicest staff, super clean and easy. "
Sayada 5-night trip
Posted 8 days ago
Courtyard by Marriott Kingston

Frequently asked questions

Searching for romantic hotels in Woodstock?
Are you in need of 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'd like to stay close to a certain attraction, you can sort by neighbourhood and proximity to top sights, so you'll be able to see everything on your list.
What's the best accommodation for a romantic holiday in Woodstock?
This Sioux Tipi is no longer available, but we have one nearby in another town! is a favourite lodge for couples, and features in-room fireplaces and kitchens.
How many romantic hotels can we expect to find in Woodstock?
Expedia has 23 romantic Woodstock hotels for you to get cosy 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, take a look at these details about year-round temperatures in Woodstock: The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Woodstock are January, February, March and April, with each month seeing an average of 17 cm 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 go off without a hitch: The closest major airport is in Hudson, NY (HCC-Columbia County), located 27.2 mi (43.7 km) from the city centre. If you'd like to venture out around the area, you may want a rental car for your journey.