Best Windham Vacation Rentals
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Guest favorite
Redwood Retreat In Windham - Pool! Tennis!
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Outdoor swimming pool
With a maximum capacity of 6 guests, the 2-bedroom Redwood Retreat - Minutes To Windham Mtn! Villa provides them with a seasonal outdoor swimming pool and access to such wellness attractions as The Windham Spa, located approximately 10 minutes away by car. This Windham holiday home boasts a terrace and a golf course, while C D Lane Park is 3.9 km away.
An array of such activities as horseback riding and mini golf is offered.
Redwood Retreat In Windham - Pool! Tennis!
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Golf centre
- Outdoor swimming pool
Redwood Retreat In Windham - Pool! Tennis!
With a maximum capacity of 6 guests, the 2-bedroom Redwood Retreat - Minutes To Windham Mtn! Villa provides them with a seasonal outdoor swimming pool and access to such wellness attractions as The Windham Spa, located approximately 10 minutes away by car. This Windham holiday home boasts a terrace and a golf course, while C D Lane Park is 3.9 km away.
An array of such activities as horseback riding and mini golf is offered.
Catskills Home, 5 Mins To Windham Mtn Resort!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Heating
- Spa & wellness centre
Located nearly 25 minutes' walk from Carole's Gift Emporium, the 2-bedroom Catskills Home, 5 Mins To Windham Mtn Resort! provides access to various tourist attractions in the vicinity. This welcoming holiday home accommodates up to 6 guests and has hire available for rental.
Catskills Home, 5 Mins To Windham Mtn Resort!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Heating
- Spa & wellness centre
Catskills Home, 5 Mins To Windham Mtn Resort!
Located nearly 25 minutes' walk from Carole's Gift Emporium, the 2-bedroom Catskills Home, 5 Mins To Windham Mtn Resort! provides access to various tourist attractions in the vicinity. This welcoming holiday home accommodates up to 6 guests and has hire available for rental.
Beautiful Windham Chalet 2 Minutes To The Mountain
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Sun terrace
4-bedroom Beautiful Windham Chalet 2 Minutes To The Mountain provides a sun deck and a golf course for guests' leisure, and is approximately a 25-minute walk from Carole's Gift Emporium. Offering badminton, this property is suitable for 10 guests.
Beautiful Windham Chalet 2 Minutes To The Mountain
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Sun terrace
Beautiful Windham Chalet 2 Minutes To The Mountain
4-bedroom Beautiful Windham Chalet 2 Minutes To The Mountain provides a sun deck and a golf course for guests' leisure, and is approximately a 25-minute walk from Carole's Gift Emporium. Offering badminton, this property is suitable for 10 guests.
Cheap Windham Vacation Rentals
High Peak Heaven: Cozy Log Cabin On 1 Acre!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Spa & wellness centre
- Terrace
Nestled about 7 km from Zoom Flume Water Park, the welcoming High Peak Heaven: Cozy Log Cabin On 1 Acre! Windham entices guests to explore various tourist destinations nearby. This 2-bedroom villa accommodates 5 guests and includes hire available for rent.
High Peak Heaven: Cozy Log Cabin On 1 Acre!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Spa & wellness centre
- Terrace
High Peak Heaven: Cozy Log Cabin On 1 Acre!
Nestled about 7 km from Zoom Flume Water Park, the welcoming High Peak Heaven: Cozy Log Cabin On 1 Acre! Windham entices guests to explore various tourist destinations nearby. This 2-bedroom villa accommodates 5 guests and includes hire available for rent.
Cozy Catskill Condo - 2 Mi To Windham Mountain Ski
- Cookware/ Kitchen utensils
- Free parking
- Flat-screen TV
- Laundry
- Spa & wellness centre
- Terrace
Staying at the 2-bedroom Cozy Catskill Condo - 2 Mi To Windham Mountain Ski villa, guests can easily reach The Windham Spa, located just 1.5 km away. The welcoming holiday home sleeps up to 6 guests and includes hire for hire.
Cozy Catskill Condo - 2 Mi To Windham Mountain Ski
- Cookware/ Kitchen utensils
- Free parking
- Flat-screen TV
- Laundry
- Spa & wellness centre
- Terrace
Cozy Catskill Condo - 2 Mi To Windham Mountain Ski
Staying at the 2-bedroom Cozy Catskill Condo - 2 Mi To Windham Mountain Ski villa, guests can easily reach The Windham Spa, located just 1.5 km away. The welcoming holiday home sleeps up to 6 guests and includes hire for hire.
Spacious Apt W/ Yard: 3 Mi To Windham Mountain
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
The welcoming 102 m² Spacious Apt W/ Yard: 3 Mi To Windham Mountain is located approximately a 10-minute drive from The Windham Spa and offers Wi-Fi for either business or leisure. The 2-bedroom apartment offers a convenient location 3.4 km from Windham Theatre.
Make your stay at Spacious Apt W/ Yard: 3 Mi To Windham Mountain more exciting by joining in hiking.
Spacious Apt W/ Yard: 3 Mi To Windham Mountain
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
Spacious Apt W/ Yard: 3 Mi To Windham Mountain
The welcoming 102 m² Spacious Apt W/ Yard: 3 Mi To Windham Mountain is located approximately a 10-minute drive from The Windham Spa and offers Wi-Fi for either business or leisure. The 2-bedroom apartment offers a convenient location 3.4 km from Windham Theatre.
Make your stay at Spacious Apt W/ Yard: 3 Mi To Windham Mountain more exciting by joining in hiking.
Pet Friendly Vacation Rentals Windham
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Top location
Townhouse W Private Deck & Mt View
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Sun terrace
To enjoy your vacation in Windham, stay at the 2-room Townhouse W Private Deck & Mt View Apartment Windham, which is only 200 metres from Windham Theatre and a mere 5 minutes on foot from Carole's Gift Emporium.
Townhouse W Private Deck & Mt View
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Sun terrace
Townhouse W Private Deck & Mt View
To enjoy your vacation in Windham, stay at the 2-room Townhouse W Private Deck & Mt View Apartment Windham, which is only 200 metres from Windham Theatre and a mere 5 minutes on foot from Carole's Gift Emporium.
Windham Retreat W/ Private Deck & Mtn Views!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Heating
Situated 4.6 km from Windham Theatre, the 2-bedroom Your Windham Fall And Winter Escape Awaits! villa provides access to numerous tourist attractions in the area. With a maximum capacity of 6 guests, this property offers parking.
Windham Retreat W/ Private Deck & Mtn Views!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Heating
Windham Retreat W/ Private Deck & Mtn Views!
Situated 4.6 km from Windham Theatre, the 2-bedroom Your Windham Fall And Winter Escape Awaits! villa provides access to numerous tourist attractions in the area. With a maximum capacity of 6 guests, this property offers parking.
Mountain Cabin With Scenic Views And Hot Tub
- Cookware/ Kitchen utensils
- Air conditioning
- Tea and coffee facilities
- Heating
- Garden area
The 2-bedroom Mountain Cabin With Scenic Views And Hot Tub Windham, located only 5 minutes' walk from Carole's Gift Emporium, can host up to 7 guests.
Mountain Cabin With Scenic Views And Hot Tub
- Cookware/ Kitchen utensils
- Air conditioning
- Tea and coffee facilities
- Heating
- Garden area
Mountain Cabin With Scenic Views And Hot Tub
The 2-bedroom Mountain Cabin With Scenic Views And Hot Tub Windham, located only 5 minutes' walk from Carole's Gift Emporium, can host up to 7 guests.
Windham Vacation Rentals Oceanfront
Condo W/ Loft: 2 Mi To Windham Mountain Ski!
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Car park
Charges may apply
- Flat-screen TV
Located 25 minutes' walk from Windham Fine Arts, Condo W/ Loft: 2 Mi To Windham Mountain Ski! villa gives access to various tourist sites in the vicinity. With a capacity for 6 guests, the 2-bedroom holiday home offers hire available for renting.
Condo W/ Loft: 2 Mi To Windham Mountain Ski!
-
Car park
Charges may apply
- Flat-screen TV
Condo W/ Loft: 2 Mi To Windham Mountain Ski!
Located 25 minutes' walk from Windham Fine Arts, Condo W/ Loft: 2 Mi To Windham Mountain Ski! villa gives access to various tourist sites in the vicinity. With a capacity for 6 guests, the 2-bedroom holiday home offers hire available for renting.
1/2 Mi To Windham Mtn: Main Street Condo
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Heating
1/2 Mi To Windham Mtn: Main Street Condo villa, located just a few steps from Windham Fine Arts, can host up to 4 guests. Located a 7-minute walk from The Windham Spa, the 2-bedroom holiday home provides Wi-Fi and private car parking.
1/2 Mi To Windham Mtn: Main Street Condo
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Heating
1/2 Mi To Windham Mtn: Main Street Condo
1/2 Mi To Windham Mtn: Main Street Condo villa, located just a few steps from Windham Fine Arts, can host up to 4 guests. Located a 7-minute walk from The Windham Spa, the 2-bedroom holiday home provides Wi-Fi and private car parking.
Mountain Blue Vista - Hot Tub, Firepit, 10 Acres, Perfect Location!
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Table tennis
- Sun terrace
The 4-bedroom Lux Estate! Hot Tub, 8 Acres, Firepit, Game Room, Private Pond, Ev, Lots Of Privacy, 10 Mins To Town Windham is located within a 7-km distance of Windham Fine Arts and has a sun deck and a picnic area to ensure a memorable stay.
There are a Jacuzzi to enhance your stay. Archery, hiking, and ping-pong are offered in the vicinity of the Windham accommodation.
Mountain Blue Vista - Hot Tub, Firepit, 10 Acres, Perfect Location!
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Table tennis
- Sun terrace
Mountain Blue Vista - Hot Tub, Firepit, 10 Acres, Perfect Location!
The 4-bedroom Lux Estate! Hot Tub, 8 Acres, Firepit, Game Room, Private Pond, Ev, Lots Of Privacy, 10 Mins To Town Windham is located within a 7-km distance of Windham Fine Arts and has a sun deck and a picnic area to ensure a memorable stay.
There are a Jacuzzi to enhance your stay. Archery, hiking, and ping-pong are offered in the vicinity of the Windham accommodation.
Windham Vacation Rentals with Private Pool
Windham Ridge Chalet
- BBQ facilities
- Free parking
- Tours/Ticket assistance
- Air conditioning
- Live entertainment
- Sun terrace
Set nearly a 25-minute walk from Windham Theatre, the 3-bedroom Windham Ridge Chalet comprises a patio and a dining area overlooking the garden. This spacious apartment is equipped with a Jacuzzi, creating a more enjoyable ambiance for guests.
Other facilities at Windham Ridge Chalet include a sunbathing terrace, a picnic area, and a golf course. If sport sounds tempting, lawn tennis, mini golf, and cycling are offered.
Windham Ridge Chalet
- BBQ facilities
- Free parking
- Tours/Ticket assistance
- Air conditioning
- Live entertainment
- Sun terrace
Windham Ridge Chalet
Set nearly a 25-minute walk from Windham Theatre, the 3-bedroom Windham Ridge Chalet comprises a patio and a dining area overlooking the garden. This spacious apartment is equipped with a Jacuzzi, creating a more enjoyable ambiance for guests.
Other facilities at Windham Ridge Chalet include a sunbathing terrace, a picnic area, and a golf course. If sport sounds tempting, lawn tennis, mini golf, and cycling are offered.
Homey Windham Condo: Hike & Ski The Catskill Mtns!
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Car park
Charges may apply
- Flat-screen TV
Offering a location approximately a 25-minute walk from Windham Theatre, welcoming Homey Windham Condo: Hike & Ski The Catskill Mtns! villa gives access to various tourist spots in the area. This 2-bedroom holiday home is suitable for 4 guests and provides hire for hire.
Homey Windham Condo: Hike & Ski The Catskill Mtns!
-
Car park
Charges may apply
- Flat-screen TV
Homey Windham Condo: Hike & Ski The Catskill Mtns!
Offering a location approximately a 25-minute walk from Windham Theatre, welcoming Homey Windham Condo: Hike & Ski The Catskill Mtns! villa gives access to various tourist spots in the area. This 2-bedroom holiday home is suitable for 4 guests and provides hire for hire.
Cozy Mtn-View Chalet < 2 Mi To Windham Slopes
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Heating
- Jacuzzi
During the stay at the welcoming Cozy Mtn-View Chalet 2 Mi To Windham Slopes, guests can indulge in a Jacuzzi or visit Windham Mountain Resort, located 3.2 km away. Located within a 10-minute drive of The Windham Spa, this 2-bedroom holiday home provides Wi-Fi and parking.
Cozy Mtn-View Chalet < 2 Mi To Windham Slopes
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Heating
- Jacuzzi
Cozy Mtn-View Chalet < 2 Mi To Windham Slopes
During the stay at the welcoming Cozy Mtn-View Chalet 2 Mi To Windham Slopes, guests can indulge in a Jacuzzi or visit Windham Mountain Resort, located 3.2 km away. Located within a 10-minute drive of The Windham Spa, this 2-bedroom holiday home provides Wi-Fi and parking.
Windham Home Near Mountain Biking & Hiking Trails!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Heating
The 2-bedroom Windham Home Near Mountain Biking & Hiking Trails! offers easy access to such tourist spots as The Windham Spa, located merely a 5-minute walk away. Providing guests with Wi-Fi and a private parking lot, this Windham holiday home is about 900 metres from Carole's Gift Emporium.
Windham Home Near Mountain Biking & Hiking Trails!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Heating
Windham Home Near Mountain Biking & Hiking Trails!
The 2-bedroom Windham Home Near Mountain Biking & Hiking Trails! offers easy access to such tourist spots as The Windham Spa, located merely a 5-minute walk away. Providing guests with Wi-Fi and a private parking lot, this Windham holiday home is about 900 metres from Carole's Gift Emporium.
The Windham A
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Terrace
Situated 3.8 km from Carole's Gift Emporium, The Windham A Villa entices guests to explore various tourist attractions in the area. This 1-bedroom holiday home hosts up to 8 guests and provides them with private parking.
The Windham A
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Mini-bar
- Terrace
The Windham A
Situated 3.8 km from Carole's Gift Emporium, The Windham A Villa entices guests to explore various tourist attractions in the area. This 1-bedroom holiday home hosts up to 8 guests and provides them with private parking.
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Great deal
Black Bear Cabin
- BBQ facilities
- Free parking
- Security
- Flat-screen TV
- Sauna
- Pool with view
Located approximately a 25-minute stroll from The Windham Spa, the 4-bedroom Black Bear Cabin Windham boasts a heated pool with a pool cover.
Black Bear Cabin has a hot tub and a sauna for relaxation along with a sundeck and a golf course for leisure. The property offers a games room for entertainment, as well as hiking, horseback riding, and cycling for sport lovers. To ensure children's entertainment, this Windham accommodation provides toys and board games.
Black Bear Cabin
- BBQ facilities
- Free parking
- Security
- Flat-screen TV
- Sauna
- Pool with view
Black Bear Cabin
Located approximately a 25-minute stroll from The Windham Spa, the 4-bedroom Black Bear Cabin Windham boasts a heated pool with a pool cover.
Black Bear Cabin has a hot tub and a sauna for relaxation along with a sundeck and a golf course for leisure. The property offers a games room for entertainment, as well as hiking, horseback riding, and cycling for sport lovers. To ensure children's entertainment, this Windham accommodation provides toys and board games.
Grand Windham Retreat W/ Fire Pit & Game Room
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Fitness centre
- Terrace
Situated 4.3 km from Carole's Gift Emporium, the welcoming Grand Windham Retreat W/ Fire Pit & Game Room villa entices guests to explore various tourist attractions in the area. This 2-bedroom holiday home hosts up to 6 guests and provides them with parking.
Grand Windham Retreat W/ Fire Pit & Game Room
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Fitness centre
- Terrace
Grand Windham Retreat W/ Fire Pit & Game Room
Situated 4.3 km from Carole's Gift Emporium, the welcoming Grand Windham Retreat W/ Fire Pit & Game Room villa entices guests to explore various tourist attractions in the area. This 2-bedroom holiday home hosts up to 6 guests and provides them with parking.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Windham, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Redwood Retreat In Windham - Pool! Tennis! |
9.4 / 10 (21 Reviews) |
From 199$ | |
| Catskills Home, 5 Mins To Windham Mtn Resort! |
8.6 / 10 (6 Reviews) |
From 156$ | |
| Beautiful Windham Chalet 2 Minutes To The Mountain |
9.1 / 10 (9 Reviews) |
From 403$ | |
| High Peak Heaven: Cozy Log Cabin On 1 Acre! |
9.4 / 10 (7 Reviews) |
From 203$ | |
| Cozy Catskill Condo - 2 Mi To Windham Mountain Ski |
8.8 / 10 (4 Reviews) |
From 194$ |
Frequently Asked Questions
Which Windham vacation rentals are ideal for families with kids?
Consider staying at the Cozy Catskill Condo and High Peak Heaven, both suitable for families. These options provide comfortable living spaces and nearby outdoor activities great for kids.
Choose accommodations that offer kitchens to prepare affordable meals and save on dining costs.
What vacation rentals near Windham Mountain are best for skiing?
The Condo W/ Loft and Beautiful Windham Chalet provide a quick 2-mile reach to Windham Mountain Ski Resort. These rentals offer cozy atmospheres for post-ski relaxation.
Book your rental during weekdays for lower prices and fewer crowds on the slopes.
Which rentals in Windham come with a pool?
Redwood Retreat In Windham offers a pool along with tennis facilities, perfect for a fun family getaway. This amenity allows for relaxing afternoons after exploring the area.
Visit in the summer when outdoor activities are in full swing to maximize your pool days.
Are there any Windham vacation rentals with hot tubs?
Mountain Cabin With Scenic Views has a hot tub that invites relaxation after a day of hiking or skiing. This feature adds a touch of luxury to your stay.
Aim for evening hours to enjoy the hot tub under the stars for a memorable experience.
Which Windham rentals offer great mountain views?
Windham Retreat W/ Private Deck & Mtn Views is perfect for stunning scenery. Guests can enjoy their mornings with coffee on the deck overlooking the mountains.
Choose a rental that faces the mountains to experience breathtaking sunrises each day.
What are some budget-friendly vacation rentals in Windham?
Catskills Home and Cozy Catskill Condo offer affordable stays while still providing comfortable amenities. They allow for enjoyable experiences without overspending.
Book in the off-season to find the best rates and fewer tourists, especially during winter or early spring.
Which rental has the best outdoor space for gatherings?
The Grand Windham Retreat has a large fire pit and game room perfect for gatherings with friends or family. This space encourages fun and interaction day or night.
Plan outdoor gatherings during warm evenings for a vibrant atmosphere with great stargazing opportunities.
What unique activities can I do while staying in Windham?
You can explore the scenic hiking trails at the Windham-Essex Jct. Trail System and Revel in amazing views. Don't miss the Windham Farmer's Market on Sundays for local goods.
Visit the farmer's market early in the morning for the freshest produce and best selection of local crafts.
What nearby attractions are worth visiting from Windham?
Consider visiting the nearby Kaaterskill Falls and the Hudson River Scenic Byway for stunning natural beauty. Both attractions are popular and provide unique experiences.
Go to Kaaterskill Falls on weekdays for fewer crowds and the best photo opportunities.
How can I easily get around Windham and its attractions?
Using a personal vehicle gives you the most flexibility to explore. However, local shuttles may connect you to Windham Mountain and other attractions during ski season.
Carpool whenever possible to reduce parking headaches and have fun with your group.