A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

Best Resorts in Windham

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Check prices for these dates

Next weekend
Jul 3 - Jul 5
In two weeks
Jul 10 - Jul 12
In one month
Jul 24 - Jul 26
In two months
Aug 21 - Aug 23
No exact matches found, but these alternatives could be just right

Recommended hotels in Windham

View from room

Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (815 reviews)
"Great place"
United States
John
$164 nightly
The price is $177
Jul 1 - Jul 2
Total with taxes and fees
Hotel Vienna
Front of property

Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (144 reviews)
"Low key but very nice. Excellent location and value."
United States
Dan
$130 nightly
The price is $140
Jul 8 - Jul 9
Total with taxes and fees
Cave Mountain Motel
Front of property

Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (133 reviews)
"A fantastic stay!"
United States
David
$135 nightly
The price is $146
Jun 24 - Jun 25
Total with taxes and fees
Antique Rose Inn Windham
Double Room, Mountain View | Exterior

Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
$160 nightly
The price is $173
Jun 24 - Jun 25
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
Interior

The Haüs Windham

The Haüs Windham
2.0 star property
Windham
7.6 out of 10, Good, (29 reviews)
"Can’t complain one bit"
United States
Christopher
$223 nightly
The price is $241
Jun 24 - Jun 25
Total with taxes and fees
The Haüs Windham
Front of property

Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (281 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
$150 nightly
The price is $162
Jun 24 - Jun 25
Total with taxes and fees
Albergo Allegria Hotel
Lushna Cabin | Free WiFi, bed sheets

Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (107 reviews)
"Gorgeous, tasteful and close to activities, restaurant is fanstastic"
United States
Andre
$209 nightly
The price is $225
Jun 25 - Jun 26
Total with taxes and fees
Eastwind Windham
Exterior

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (45 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
$127 nightly
The price is $137
Jun 24 - Jun 25
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Exterior

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (60 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
$203 nightly
The price is $219
Jun 24 - Jun 25
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Exterior

The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (354 reviews)
"It was so comfortable to stay there, we skied and was the perfect place to stay for a couple nights. "
United States
Nicoletta
$137 nightly
The price is $148
Jun 25 - Jun 26
Total with taxes and fees
The Winwood Condominiums
Hair dryer, towels, soap, shampoo

King Suite · Full Kitchen · Fireplace · Private Deck · Sleeps 4

King Suite · Full Kitchen · Fireplace · Private Deck · Sleeps 4
Windham
7.6 out of 10, Good, (5 reviews)
"Excellent accommodations, close to everything you could need. My wife and I had a perfect evening "
United States
Anthony M.
$208 nightly
The price is $236
Jun 24 - Jun 25
Total with taxes and fees
King Suite · Full Kitchen · Fireplace · Private Deck · Sleeps 4
Terrace/patio

Tiny House on Walnut Grove

Tiny House on Walnut Grove
Ashland
4.0 out of 10, (2 reviews)
"Many problems with this listing, first the fire alarm was low on battery, I had to physically climb to reach the smoke detector to detach and remove the battery, a sharp beeping noise went off every 90 seconds and we wouldn’t have been able to sleep without stopping it. There were no spare batteries to change. There were spiders everywhere. My friend used the shower and saw 11 of them moving around the ceiling. They were in the main bed and on the counter and sink as well. The tenant was nice...
United States
Trevor C.
$263 nightly
The price is $284
Jun 24 - Jun 25
Total with taxes and fees
Tiny House on Walnut Grove
Exterior

Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"House is cozy and has everything you need. We enjoyed our stay."
United States
William H.
$491 nightly
The price is $530
Jul 21 - Jul 22
Total with taxes and fees
Pines Vignette • Modern 3BR Home in Windham
Dining

2 Min Walk to Windham Town | Hot Tub | Fire Pit

2 Min Walk to Windham Town | Hot Tub | Fire Pit
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Great location, perfect layout and responsive host! Thanks for hosting - would gladly stay again. "
United States
Melissa R.
$483 nightly
The price is $522
Jun 25 - Jun 26
Total with taxes and fees
2 Min Walk to Windham Town | Hot Tub | Fire Pit
TV, fireplace

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (7 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
$493 nightly
The price is $532
Jun 24 - Jun 25
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Exterior

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Windham
$599 nightly
The price is $646
Jul 21 - Jul 22
Total with taxes and fees
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Hair dryer, towels, soap, shampoo

Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn

Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn
Windham
$166 nightly
The price is $188
Jun 24 - Jun 25
Total with taxes and fees
Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn
In-room safe, bed sheets

Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway

Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway
Windham
8.0 out of 10, Very Good, (2 reviews)
"This was a unique and fun VRBO experience. The cabin was cozy and comfortable.So delightful to wake up to deer walking right by the window! Absolutely a gem of a property!"
United States
Erin J.
$334 nightly
The price is $379
Jun 29 - Jun 30
Total with taxes and fees
Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway
Interior

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Ashland
9.2 out of 10, Wonderful, (5 reviews)
"Great place to stay very accommodating more than expected "
United States
Julia M.
$472 nightly
The price is $510
Jun 24 - Jun 25
Total with taxes and fees
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Terrace/patio

The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham

The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Ashland
$654 nightly
The price is $706
Jun 24 - Jun 25
Total with taxes and fees
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
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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Top Windham Hotel Reviews

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

8/10 Good
"My wife and I always enjoy staying here. Great location and nice establishment."
Eddie 2-night trip
Posted 13 hours ago
Kaatskill Mountain Club & Condos by Vail Resorts

Find out more about Windham

Windham Resorts information

Number of reviews
1,575
Accommodation
0 Resorts
Lowest Price
$137
Highest Price
$706

Frequently asked questions

What can I expect from a resort vacation in Windham?
You deserve some time off, and a resort is the ideal place to indulge in all the amenities and services you need for a relaxing stay in Windham. One of the comfortable resorts in the area could be just what you're looking for, whether you want great restaurants on site, shopping possibilities, or fun activities to try.
What can I do in Windham?
Travelers like the mountain scenery in Windham, and enjoy its skiing and other winter sports. Grab your golf clubs for a game at Windham Country Club, or head for the ski slopes at Windham Mountain Resort. For more to see in the area, you can spend time at Windham Vineyards and Winery or Catskill State Park.
What's the seasonal weather like in Windham?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Windham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Windham?
Fly into Hudson, NY (HCC-Columbia County), which is located 27.6 mi (44.4 km) away from the heart of the city. If you'd like to venture out around the area, consider renting a car to take in more sights.

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