Hotels near Windham Vineyards and Winery Windham
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Cave Mountain Motel
Cave Mountain Motel
2.5 star property
2.4 mi from Windham Vineyards and Winery
- Free parking
- Free WiFi
- Air conditioning
- 24/7 front desk
- Non-smoking
9.4 out of 10, Exceptional, (126)
9.4/10
Exceptional
(126)
- Mountain retreat offers tranquil mornings with garden breakfasts, outdoor lounging spaces, and the smoky allure of barbecue grills
Cave Mountain Motel highlights
The Cave Mountain Motel sits among peaks, serving up serenity with a side of free breakfast buffet. Guests tap into Wi-Fi from their rooms, find their zen on outdoor furniture, or channel their inner grill master at the barbecue station.
The Cave Mountain Motel sits among peaks, serving up serenity with a side of free breakfast buffet. Guests tap into Wi-Fi from their rooms, find their zen on outdoor furniture, or channel their inner grill master at the barbecue station.
$129 nightly
The price is $139
$139 total
Jun 15 - Jun 16
Total includes taxes and fees
Silas House
Silas House
3.0 star property
5.9 mi from Windham Vineyards and Winery
- Free parking
- Free WiFi
- Non-smoking
- Ski facilities
10.0 out of 10, Exceptional, (11)
10.0/10
Exceptional
(11)
- Mountain retreat offers a blend of cozy comfort and natural beauty, with a firepit for evening relaxation and fresh air for daytime adventures
Silas House highlights
Silas House sits amid mountain scenery, providing a laid-back vibe with practical perks like continental breakfast and WiFi. Guests can chill by the firepit, wander through the garden, or dive into a book from the in-house library.
Silas House sits amid mountain scenery, providing a laid-back vibe with practical perks like continental breakfast and WiFi. Guests can chill by the firepit, wander through the garden, or dive into a book from the in-house library.
$181 nightly
The price is $196
$196 total
Jun 17 - Jun 18
Total includes taxes and fees
Albergo Allegria Hotel & Breakfast Restaurant
Albergo Allegria Hotel & Breakfast Restaurant
3.5 star property
4.4 mi from Windham Vineyards and Winery
- Free parking
- Free WiFi
- Restaurant
- Air conditioning
- Non-smoking
- Ski facilities
9.6 out of 10, Exceptional, (261)
9.6/10
Exceptional
(261)
- A mountain retreat where golf clubs meet fireplace crackles, and nature's beauty unfolds in a garden with views that'll make you forget to blink
What guests liked
- Breakfast was consistently described as delicious, fantastic, and outstanding by multiple guests.
Albergo Allegria Hotel & Breakfast Restaurant highlights
Near Windham Mountain Resort, this hotel offers serenity and adventure. Guests can tee off, bike scenic routes, or soak up the sun on the terrace. As the day ends, the lobby fireplace beckons with warmth and strong Wi-Fi for uploading envy-inducing garden shots.
Near Windham Mountain Resort, this hotel offers serenity and adventure. Guests can tee off, bike scenic routes, or soak up the sun on the terrace. As the day ends, the lobby fireplace beckons with warmth and strong Wi-Fi for uploading envy-inducing garden shots.
$134 nightly
The price is $145
$145 total
Jun 15 - Jun 16
Total includes taxes and fees
Eastwind Windham
Eastwind Windham
2.0 star property
4.3 mi from Windham Vineyards and Winery
- Pet friendly
- Free parking
- Free WiFi
- Air conditioning
- Bar
- Non-smoking
9.4 out of 10, Exceptional, (56)
9.4/10
Exceptional
(56)
- Morning coffee kicks off a day of exploration, capped by evening relaxation at a cozy bar nestled in the heart of Windham
Eastwind Windham highlights
Eastwind Windham greets visitors with a laid-back vibe and practical perks. Guests start their day with continental breakfast, surf the web via in-room WiFi, and park for free. The lobby's always stocked with coffee and tea, perfect for a quick pick-me-up between adventures.
Eastwind Windham greets visitors with a laid-back vibe and practical perks. Guests start their day with continental breakfast, surf the web via in-room WiFi, and park for free. The lobby's always stocked with coffee and tea, perfect for a quick pick-me-up between adventures.
$229 nightly
The price is $247
$247 total
Jun 15 - Jun 16
Total includes taxes and fees
Hotel Vienna
Hotel Vienna
2.5 star property
4.6 mi from Windham Vineyards and Winery
- Pool
- Free breakfast
- Pet friendly
- Free parking
- Free WiFi
- Connecting rooms available
9.2 out of 10, Wonderful, (569)
9.2/10
Wonderful
(569)
- Stargazing by the firepit, teeing off on 18 holes, or recharging in the indoor pool: this hotel offers a trifecta of relaxation
What guests liked
- Delicious breakfast options, including fresh pastries, coffee, and juices, were available throughout the day.
- The pool was clean, well-maintained, and perfect for relaxing with temperatures around 80°.
- The property is extremely welcoming to pets, allowing them in all common areas.
Hotel Vienna highlights
Hotel Vienna, near Windham Country Club, offers serenity with continental breakfast. The garden terrace's firepit beckons, and the indoor pool is a post-adventure sanctuary. Free WiFi and bike rentals cater to the connected explorer and pedal-powered wanderer alike.
Hotel Vienna, near Windham Country Club, offers serenity with continental breakfast. The garden terrace's firepit beckons, and the indoor pool is a post-adventure sanctuary. Free WiFi and bike rentals cater to the connected explorer and pedal-powered wanderer alike.
$140 nightly
The price is $152
$152 total
Jun 23 - Jun 24
Total includes taxes and fees
Antique Rose Inn Windham
Antique Rose Inn Windham
3.0 star property
5.3 mi from Windham Vineyards and Winery
- Free breakfast
- Free parking
- Free WiFi
- Air conditioning
- 24/7 front desk
9.0 out of 10, Wonderful, (118)
9.0/10
Wonderful
(118)
- Skiers find their happy place at this cozy inn, where hearty breakfasts and convenient shuttle service set the stage for epic days on the slopes
What guests liked
- Delicious breakfast was made to order at a convenient time, accommodating various dietary needs and preferences.
Antique Rose Inn Windham highlights
This charming retreat near Windham Country Club caters to snow enthusiasts and relaxation seekers. Guests enjoy a full breakfast, sunny terrace, garden strolls, in-room WiFi, and a ski shuttle to nearby runs.
This charming retreat near Windham Country Club caters to snow enthusiasts and relaxation seekers. Guests enjoy a full breakfast, sunny terrace, garden strolls, in-room WiFi, and a ski shuttle to nearby runs.
$135 nightly
The price is $146
$146 total
Jun 16 - Jun 17
Total includes taxes and fees
Winwood Condominiums by Windham Mountain Club
Winwood Condominiums by Windham Mountain Club
3.0 star property
3.7 mi from Windham Vineyards and Winery
- Pool
- Free parking
- Free WiFi
- Laundry facilities
- 24/7 front desk
- Child-friendly activities
8.6 out of 10, Excellent, (322)
8.6/10
Excellent
(322)
- Winter wonderland meets indoor comfort at this mountain retreat, where snowflakes dance outside as guests unwind by the pool or play billiards
Winwood Condominiums by Windham Mountain Club highlights
Winwood Inn & Condominiums offers a scenic escape for families and outdoor enthusiasts. Guests can tee off at the 18-hole golf course, enjoy a sports massage at the spa, or challenge each other in the arcade. A free ski shuttle and self-parking cater to adventure seekers.
Winwood Inn & Condominiums offers a scenic escape for families and outdoor enthusiasts. Guests can tee off at the 18-hole golf course, enjoy a sports massage at the spa, or challenge each other in the arcade. A free ski shuttle and self-parking cater to adventure seekers.
$159 nightly
The price is $172
$172 total
Jun 15 - Jun 16
Total includes taxes and fees
Mountain Treasure B&B
Mountain Treasure B&B
3.0 star property
7.1 mi from Windham Vineyards and Winery
- Free parking
- Free WiFi
- Air conditioning
9.4 out of 10, Exceptional, (269)
9.4/10
Exceptional
(269)
- Mornings begin with a hearty breakfast, setting the stage for a day of mountain exploration and natural wonders
What guests liked
- Breakfast was consistently described as delicious, wonderful, and amazing with many guests praising the host's home-cooked meals.
Mountain Treasure B&B highlights
This mountain B&B serves as a quiet getaway, offering full breakfasts and garden serenity. Guests can soak in scenic vistas from the terrace, stay connected via WiFi, and immerse themselves in the surrounding natural beauty.
This mountain B&B serves as a quiet getaway, offering full breakfasts and garden serenity. Guests can soak in scenic vistas from the terrace, stay connected via WiFi, and immerse themselves in the surrounding natural beauty.
$143 nightly
The price is $155
$155 total
Jun 15 - Jun 16
Total includes taxes and fees
Xenia Resort
Xenia Resort
2.5 star property
6.8 mi from Windham Vineyards and Winery
- Spa
- Free parking
- Free WiFi
- Restaurant
- Non-smoking
9.0 out of 10, Wonderful, (53)
9.0/10
Wonderful
(53)
- Mountain retreat offers Thai massages, fireside relaxation, and late-night pool games with scenic views for the perfect unwind
What guests liked
- Delicious breakfast options were available at the property.
Xenia Resort highlights
Xenia Resort offers a mountain escape with Thai massages and a cozy fireplace. Enjoy evening entertainment with a billiards table, plus practical perks like free parking and luggage storage. The breakfast is worth writing home about.
Xenia Resort offers a mountain escape with Thai massages and a cozy fireplace. Enjoy evening entertainment with a billiards table, plus practical perks like free parking and luggage storage. The breakfast is worth writing home about.
$145 nightly
The price is $157
$157 total
Jun 15 - Jun 16
Total includes taxes and fees
Wylder Hotel Windham
Wylder Hotel Windham
3.5 star property
4.3 mi from Windham Vineyards and Winery
- Pool
- Pet friendly
- Free parking
- Free WiFi
- Restaurant
- Air conditioning
8.4 out of 10, Very Good, (58)
8.4/10
Very Good
(58)
- Cozy up by the lobby fireplace, shoot pool with friends, or venture into nearby nature reserves. Breakfast here is a delicious start to the day.
Wylder Hotel Windham highlights
In the heart of Windham, this hotel offers a charming retreat. The lobby fireplace sets a warm tone, while Babblers Restaurant serves up happy hour treats. Guests can connect to WiFi, cool off in the seasonal outdoor pool, or challenge friends to a game of billiards.
In the heart of Windham, this hotel offers a charming retreat. The lobby fireplace sets a warm tone, while Babblers Restaurant serves up happy hour treats. Guests can connect to WiFi, cool off in the seasonal outdoor pool, or challenge friends to a game of billiards.
$191 nightly
The price is $206
$206 total
Jun 16 - Jun 17
Total includes taxes and fees
Black Bear Lodge
Black Bear Lodge
2.5 star property
6.8 mi from Windham Vineyards and Winery
- Pet friendly
- Free parking
- Free WiFi
- Non-smoking
9.0 out of 10, Wonderful, (111)
9.0/10
Wonderful
(111)
- Cozy lodge offers a serene retreat with modern comforts, including lobby TV and hassle-free parking for guests seeking a low-key escape
What guests liked
- Complimentary breakfast was a pleasant and satisfying start to the day.
Black Bear Lodge highlights
Black Bear Lodge blends comfort with simplicity. Guests can stay connected with in-room WiFi while enjoying a smoke-free environment. The lobby TV provides a touch of home, and free self-parking adds convenience to this tranquil getaway.
Black Bear Lodge blends comfort with simplicity. Guests can stay connected with in-room WiFi while enjoying a smoke-free environment. The lobby TV provides a touch of home, and free self-parking adds convenience to this tranquil getaway.
$149 nightly
The price is $161
$161 total
Jun 15 - Jun 16
Total includes taxes and fees
The Colonial Motel
The Colonial Motel
2.5 star property
9.7 mi from Windham Vineyards and Winery
- Pool
- Pet friendly
- Free parking
- Free WiFi
- Air conditioning
9.4 out of 10, Exceptional, (351)
9.4/10
Exceptional
(351)
- Nature's playground awaits at this cozy motel, where sun-drenched loungers and friendly staff set the stage for memorable adventures
What guests liked
- The pool was refreshing, clean, and a super bonus on a hot summer day with chairs and toys also perfectly clean and new.
The Colonial Motel highlights
Tucked in Mine Kill State Park, the Colonial Motel offers a laid-back escape. Guests can cool off in the seasonal outdoor pool, stay connected with in-room WiFi, or venture out to soak in the scenic surroundings. The helpful staff consistently earns praise from visitors.
Tucked in Mine Kill State Park, the Colonial Motel offers a laid-back escape. Guests can cool off in the seasonal outdoor pool, stay connected with in-room WiFi, or venture out to soak in the scenic surroundings. The helpful staff consistently earns praise from visitors.
$89 nightly
The price is $98
$98 total
Jun 17 - Jun 18
Total includes taxes and fees
Moore's Motel
Moore's Motel
2.5 star property
6.7 mi from Windham Vineyards and Winery
- Pool
- Free parking
- Free WiFi
8.6 out of 10, Excellent, (144)
8.6/10
Excellent
(144)
- A laid-back escape where guests can swim in the afternoon sun, grill under the stars, and soak up the natural surroundings
Moore's Motel highlights
Moore's Motel offers a tranquil retreat amidst gardens. Visitors can stay connected with in-room WiFi, take a dip in the outdoor pool, or fire up the barbecue grills. Free self-parking adds to the hassle-free experience of this relaxed getaway.
Moore's Motel offers a tranquil retreat amidst gardens. Visitors can stay connected with in-room WiFi, take a dip in the outdoor pool, or fire up the barbecue grills. Free self-parking adds to the hassle-free experience of this relaxed getaway.
$120 nightly
The price is $130
$130 total
Jun 15 - Jun 16
Total includes taxes and fees
Kaatskill Mountain Club at Hunter Mountain
Kaatskill Mountain Club at Hunter Mountain
2.0 star property
10.1 mi from Windham Vineyards and Winery
- Pool
- Free WiFi
- Restaurant
- Laundry facilities
- 24/7 front desk
- Non-smoking
9.2 out of 10, Wonderful, (238)
9.2/10
Wonderful
(238)
- Bask by the warmth of a cozy lobby fire while enjoying top-notch hospitality nearby stunning natural beauty.
What guests liked
- The pool area was a highlight, with many guests praising its relaxing and enjoyable experience.
- The hot tubs were a great amenity, providing a refreshing and relaxing experience for guests.
- The on-site restaurant, Van Winkle's, offered outstanding food and excellent service.
Kaatskill Mountain Club at Hunter Mountain highlights
Nestled near Hunter Mountain, Kaatskill Mountain Club at Hunter Mountain is a haven of relaxation. Enjoy the warm ambiance by the lobby fireplace, indulge in American cuisine at Van Winkles restaurant, or unwind in the steam room and sauna. The outdoor pool and electric car charging station add to your comfort. With luggage storage, an elevator, and free WiFi available throughout your stay.
Nestled near Hunter Mountain, Kaatskill Mountain Club at Hunter Mountain is a haven of relaxation. Enjoy the warm ambiance by the lobby fireplace, indulge in American cuisine at Van Winkles restaurant, or unwind in the steam room and sauna. The outdoor pool and electric car charging station add to your comfort. With luggage storage, an elevator, and free WiFi available throughout your stay.
$212 nightly
The price is $229
$229 total
Jun 18 - Jun 19
Total includes taxes and fees
Hunter Lodge, a Bluebird by Lark
Hunter Lodge, a Bluebird by Lark
3.0 star property
10.8 mi from Windham Vineyards and Winery
- Free breakfast
- Pet friendly
- Free parking
- Free WiFi
- Restaurant
- Connecting rooms available
9.2 out of 10, Wonderful, (652)
9.2/10
Wonderful
(652)
What guests liked
- The on-site restaurant and tavern offered delicious meals and convenient dining options with a great atmosphere.
$154 nightly
The price is $166
$166 total
Jun 17 - Jun 18
Total includes taxes and fees
Beds on Clouds
Beds on Clouds
3.0 star property
3.5 mi from Windham Vineyards and Winery
- Free parking
- Free WiFi
- Air conditioning
7.4 out of 10, Good, (67)
7.4/10
Good
(67)
- A tranquil escape where relaxation and adventure coexist: mini-golf challenges, garden serenity, and nearby cycling await the intrepid traveler
Beds on Clouds highlights
Beds on Clouds lives up to its name, offering a peaceful retreat with a blend of zen and activity. Enjoy manicures and massages at the on-site spa, play mini-golf for fun, stay connected with free Wi-Fi, and explore locally with complimentary bike rentals.
Beds on Clouds lives up to its name, offering a peaceful retreat with a blend of zen and activity. Enjoy manicures and massages at the on-site spa, play mini-golf for fun, stay connected with free Wi-Fi, and explore locally with complimentary bike rentals.
$206 nightly
The price is $222
$222 total
Jun 13 - Jun 14
Total includes taxes and fees
The Haüs Windham
The Haüs Windham
2.0 star property
4.7 mi from Windham Vineyards and Winery
- Free parking
- Free WiFi
- Connecting rooms available
- Air conditioning
4.0 out of 10, (1)
4.0/10
(1)
- Mountain getaway meets modern convenience at the foot of Windham's slopes, where barbecue grills sizzle and WiFi keeps you connected
The Haüs Windham highlights
The Haüs Windham sits a stone's throw from Windham Mountain Resort, offering a cozy base camp for adventurers. Guests can fire up the grill for an impromptu cookout, surf the web from their rooms, and forget about parking hassles with the free lot out front.
The Haüs Windham sits a stone's throw from Windham Mountain Resort, offering a cozy base camp for adventurers. Guests can fire up the grill for an impromptu cookout, surf the web from their rooms, and forget about parking hassles with the free lot out front.
$181 nightly
The price is $195
$195 total
Jun 16 - Jun 17
Total includes taxes and fees
The Perch Hotel
The Perch Hotel
2.0 star property
8 mi from Windham Vineyards and Winery
- Free parking
- Free WiFi
- Air conditioning
10.0 out of 10, Exceptional, (2)
10.0/10
Exceptional
(2)
$218 nightly
The price is $235
$235 total
Jul 8 - Jul 9
Total includes taxes and fees
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.
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.
Other landmarks in Windham
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?
Huntersfield State Forest
You can take time to visit Huntersfield State Forest during your travels to Windham. Discover the mountain views and coffeehouses in this relaxing area.
Ashland Park
Explore the great outdoors at Ashland Park, a lovely green space in Windham. Discover the mountain views and coffeehouses in this relaxing area.
Windham Mountain Resort
Skiers and snowboarders might want to test out the slopes at Windham Mountain Resort, a skiing spot located 1.2 mi (1.9 km) from central Windham. If you master the slopes, Hunter Mountain and Mountain Trails Cross Country Ski and Snowshoe Center are also just a short drive away.
Windham Country Club
You might want to practice your swing at Windham Country Club, a golf course located 1 mi (1.6 km) from central Windham. Windham has other activities you might want to enjoy such as Hunter Mountain.
Frequently asked questions
What are the best hotels near Windham Vineyards and Winery?
- Guests love staying at Albergo Allegria Hotel & Breakfast Restaurant, which is a bed & breakfast near Windham Vineyards and Winery.
- Beds on Clouds is also well reviewed by travelers and is 12 minutes away by car.
- In fact, you’ll have plenty of options to choose from with 2,590 hotels, vacation rentals, and other accommodation options in the area.
How much does it cost to stay in a hotel near Windham Vineyards and Winery?
On Hotels.com, you can find a variety of room prices depending on when and where you plan to go. Simply sort by price on the search results and filter by your preferred criteria to find the best options for you and your budget.
- Search for the lowest price per night $98
What cheap hotels are close to Windham Vineyards and Winery?
- Winwood Inn & Condominiums is a reasonably-priced hotel near Windham Vineyards and Winery and offers free RV/bus/truck parking, a free ski shuttle, and free in-room WiFi.
- Hotel Vienna is another low-cost option 14 minutes away by car.
Can I find hotels close to Windham Vineyards and Winery that are fully refundable?
Yes, you’ll find hotels with refundable room rates, but be sure to check the cancellation deadline before you book. To find refundable rates, use the “Fully refundable” filter when you search for hotels.
- A couple of highly rated hotels near Windham Vineyards and Winery that offer these rates are Wylder Hotel Windham and Albergo Allegria Hotel & Breakfast Restaurant.
What are the best romantic hotels near Windham Vineyards and Winery?
- If you are looking for a romantic stay, Amazing Views, Away from it all! offers ski-in/ski-out access. It’s a 25-minute drive from Windham Vineyards and Winery.
- Abigail’s Country House. 2 minutes To Skiing. Swimming, Hiking very close by. is another great choice, and it’s 30 minutes away by car.
What are the best hotels close to Windham Vineyards and Winery with free breakfast?
- Start your day nourished with a free buffet breakfast at Cave Mountain Motel, which is a short 8-minute drive from Windham Vineyards and Winery.
- Hotel Vienna is also a recommended place to stay with a free continental breakfast. It’s 14 minutes away by car.
Which hotels near Windham Vineyards and Winery have rooms with great views?
- Enjoy rooms with garden or mountain view at Beds on Clouds, which is a short 12-minute drive from Windham Vineyards and Winery.
- Also recommended is Georgian Garden Inn, which offers rooms with views.
What are the best family hotels close to Windham Vineyards and Winery?
- The entire family will enjoy a stay at Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge which offers children’s books, an arcade/game room, and a barbecue grill. Windham Vineyards and Winery is 12 minutes away by car.
- Also consider Wylder Hotel Windham as another great choice for your family’s trip.
What are the best luxury hotels near Windham Vineyards and Winery?
- Indulge yourself when you stay at Urban Cowboy Lodge, which is within reach of Windham Vineyards and Winery and offers a sauna and deep-tissue massages.
- Another up-scale property is AutoCamp Catskills, which is in the larger area.
What are the best hotels near Windham Vineyards and Winery with free parking?
- Drive and park with ease when you stay at Cave Mountain Motel, which offers free parking. You’ll be a short 8-minute drive from Windham Vineyards and Winery.
- Beds on Clouds also has free parking and is 12 minutes away by car.
What are the best hotels near Windham Vineyards and Winery with a pool?
- If swimming is at the top of your list, 1828 Farmhouse Country Estate in The Heart of The Catskill Mountains has an outdoor pool. Windham Vineyards and Winery is a 21-minute drive from the hotel.
- Another great choice for a hotel with a pool is The Country Place Resort - Home of Zoom Flume Water Park.
What cheap motels can I book close to Windham Vineyards and Winery?
- To stay economically near Windham Vineyards and Winery, you can book Black Bear Lodge, which offers parking and free in-room WiFi.
- Another inexpensive motel nearby to consider is The Colonial Motel.
What are the best things to see and do around my hotel near Windham Vineyards and Winery?
- Before or after your visit to Windham Vineyards and Winery, you can check out nearby sights like Catskill Mountains, Hunter Mountain, and Windham Mountain Resort.
- Bard College, Kaaterskill Falls, and Howe Caverns are other places to visit in the area.
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