The Best Hotels Closest to Windham Vineyards and Winery in Windham for 2026

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Our top choices for Windham Vineyards and Winery hotels

A log cabin with a deck, outdoor seating, and a view of a forest.

1. Hotel Vienna

7.4 km from Windham Vineyards and Winery

Hongtao

₩186,402 total

includes taxes & fees

Nov 23 - Nov 24

A covered porch with outdoor seating, a staircase, and potted plants.

2. The Colonial Motel

15.6 km from Windham Vineyards and Winery

Eric

₩131,643 total

includes taxes & fees

Nov 25 - Nov 26

A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

3. Hunter Lodge, a Bluebird by Lark

17.3 km from Windham Vineyards and Winery

Marina

₩221,486 total

includes taxes & fees

Nov 22 - Nov 23

A large, two-story house with multiple porches and string lights.

4. Albergo Allegria Hotel

7.1 km from Windham Vineyards and Winery

Roy

₩252,042 total

includes taxes & fees

Nov 23 - Nov 24

A multi-story building with outdoor seating and a stone-paved patio.

5. Kaatskill Mountain Club & Condos by Vail Resorts

16.3 km from Windham Vineyards and Winery

Nabeel

₩272,063 total

includes taxes & fees

Nov 23 - Nov 24

A sign for Cave Mountain Motel with a rustic stone wall and greenery.

6. Cave Mountain Motel

3.8 km from Windham Vineyards and Winery

Nancy

₩201,634 total

includes taxes & fees

Nov 15 - Nov 16

A wooden cabin with a triangular roof, a wooden door, and a bench outside.

7. Eastwind Windham

6.9 km from Windham Vineyards and Winery

Danica

₩374,940 total

includes taxes & fees

Nov 29 - Nov 30

A two-story building with a balcony, surrounded by well-maintained lawns and trees.

8. The Winwood Condominiums

6 km from Windham Vineyards and Winery

Zihe

₩245,151 total

includes taxes & fees

Nov 15 - Nov 16

A park with Adirondack chairs and a table, surrounded by trees.

9. Mountain Treasure B&B

11.4 km from Windham Vineyards and Winery

Daniel

₩240,800 total

includes taxes & fees

Nov 15 - Nov 16

A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

10. Wylder Hotel Windham

6.9 km from Windham Vineyards and Winery

Daniela

₩354,573 total

includes taxes & fees

Nov 23 - Nov 24

A two-story house with a wrap-around porch, a steeply pitched roof, and a small tower-like structure on the roof.

11. Antique Rose Inn Windham

8.5 km from Windham Vineyards and Winery

David

₩195,831 total

includes taxes & fees

Nov 16 - Nov 17

Two white Adirondack chairs in a forest with fallen leaves.

12. Black Bear Lodge

10.9 km from Windham Vineyards and Winery

Adam

₩216,139 total

includes taxes & fees

Nov 15 - Nov 16

A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

13. Jimmy OConnors Windham Mountain Inn

6.3 km from Windham Vineyards and Winery

Robin

₩215,414 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with lounge chairs and potted plants.

14. Moore's Motel

10.8 km from Windham Vineyards and Winery

Marika

₩174,072 total

includes taxes & fees

Nov 12 - Nov 13

A bedroom with a large window, a bed, and a view of a forest.

15. The Haüs Windham

7.6 km from Windham Vineyards and Winery

Erica

₩427,055 total

includes taxes & fees

Nov 16 - Nov 17

16. Windham NY Escape

8.4 km from Windham Vineyards and Winery

Miguel

₩728,418 total

includes taxes & fees

Nov 16 - Nov 17

View all properties

Compare popular hotels close to Windham Vineyards and Winery

Property	Property class	Guest rating
Hotel Vienna	3.0 star property	9.4 Exceptional 910 reviews	View
The Colonial Motel	2.5 star property	9.6 Exceptional 504 reviews	View
Hunter Lodge, a Bluebird by Lark	3.0 star property	9.2 Wonderful 1,012 reviews	View
Albergo Allegria Hotel	3.5 star property	9.6 Exceptional 289 reviews	View
Kaatskill Mountain Club & Condos by Vail Resorts	2.0 star property	9.2 Wonderful 452 reviews	View

Hotels recommended for families near Windham Vineyards and Winery

Eastwind Windham

Windham

₩374,940 total

includes taxes & fees

Nov 29 - Nov 30

Other attractions near Windham Vineyards and Winery

Ashland Town Hall

Ashland Town Hall is just one of the places to see in Ashland, so why not enjoy the other things to explore during your travels?

See properties

Top Windham Vineyards and Winery Hotel Reviews

Albergo Allegria Hotel

Windham

10/10 Excellent

NH couple

The Colonial Motel

Grand Gorge

10/10 Excellent

Step back in time when a place to stay was charming, clean and had an owner who was actually on property and cared about your stay and well being. If you’re looking for the above and a little mystic, look no further. This place has history that comes along with the beautiful well appointed room. Just an all out classy mix of antique furnishings as well as modern touches like an internet connection that works, in room Keurig coffee maker , comfortable bed and clean bathroom. Our only regret was...

Paula

A room with a view of a landscape through a window, a chair, a table with a laptop, and a bed with books on it.

The Perch Hotel

East Windham

10/10 Excellent

A Hidden Gem with Million-Dollar Views! We had such a magical stay at The Perch Hotel in East Windham! The view alone is worth the trip — on a clear day, you can see FIVE states from the property. Yes, five! It’s absolutely breathtaking and made for the perfect backdrop to relax and soak in the Catskills air. The vibe of the hotel is something special — a perfect blend of modern comfort and mid-century charm that instantly transported me back to the golden era of Catskill tourism. It’s stylish...

Emmi

Jimmy OConnors Windham Mountain Inn

Windham

10/10 Excellent

I have stayed at well over a dozen motels, hotels, lodges, resorts over my time in the Catskills. This was by far one of my favorites and is almost certainly going to become my regular resting spot. The location is premium, with it located in the heart of the Catskills, and not far from most attractions and hikes. The bar itself serves great food and drinks, and Sean and the staff are a delight to speak to. The room is clean, well maintained, and the cleaning staff do a great job each day. Most...

Asher

Mountain Treasure B&B

Maplecrest

10/10 Excellent

Alina

Eastwind Windham

Windham

10/10 Excellent

Danica

A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

Shandaken Inn

Shandaken

10/10 Excellent

Anonymous traveler

Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

10/10 Excellent

Joseph

Frequently Asked Questions

What's the area like around Windham Vineyards and Winery?

Windham Vineyards and Winery is located in an area of Windham that travelers like for its mountain views, coffeehouses, and skiing. If you're looking for a convenient place to stay, check out the 8 hotels and other accommodations you'll find within a mile.

What's the best hotel to stay near Windham Vineyards and Winery?

Located 2.4 mi (3.8 km) from Windham Vineyards and Winery, Cave Mountain Motel is one of the top choices for your stay based on our traveler data.

How many hotels will I be able to find near Windham Vineyards and Winery?

Expedia has 8 hotels and other accommodations within a mile from Windham Vineyards and Winery.

If I need to cancel the hotel reservation for my stay near Windham Vineyards and Winery, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel and receive a refund within a 24-hour period of your booking. Enter your dates, click on "Search", then you can use the "fully refundable" filter to review the best deals available near Windham Vineyards and Winery.

Where can I learn more about changing or cancelling my trip in the area near Windham Vineyards and Winery?

For additional details about rescheduling or cancelling your stay near Windham Vineyards and Winery, go to https://www.expedia.com/service/.

Find hotels near Windham Vineyards and Winery, Windham from ₩119,675

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Be picky

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Our top choices for Windham Vineyards and Winery hotels

1. Hotel Vienna

2. The Colonial Motel

3. Hunter Lodge, a Bluebird by Lark

4. Albergo Allegria Hotel

5. Kaatskill Mountain Club & Condos by Vail Resorts

6. Cave Mountain Motel

7. Eastwind Windham

8. The Winwood Condominiums

9. Mountain Treasure B&B

10. Wylder Hotel Windham

11. Antique Rose Inn Windham

12. Black Bear Lodge

13. Jimmy OConnors Windham Mountain Inn

14. Moore's Motel

15. The Haüs Windham

16. Windham NY Escape

Compare popular hotels close to Windham Vineyards and Winery

Hotels recommended for families near Windham Vineyards and Winery

Eastwind Windham

Other attractions near Windham Vineyards and Winery

Ashland Town Hall

Top Windham Vineyards and Winery Hotel Reviews

Albergo Allegria Hotel

10/10 Excellent

Frequently Asked Questions

What's the area like around Windham Vineyards and Winery?

What's the best hotel to stay near Windham Vineyards and Winery?

How many hotels will I be able to find near Windham Vineyards and Winery?

If I need to cancel the hotel reservation for my stay near Windham Vineyards and Winery, will I receive a refund?

Where can I learn more about changing or cancelling my trip in the area near Windham Vineyards and Winery?