Windham Vacation Rentals & Ski-in/Ski-out Homes
10.0
Exceptional
(107 Reviews)
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $200/Night
For 7 Nights US $1,399
10.0
Exceptional
(3 Reviews)
1905.21 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Ski Chalet
- Balcony/Terrace
- Parking
- Internet
US $254/Night
For 7 Nights US $1,779
9.0
Exceptional
(129 Reviews)
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Skiing
- Balcony/Terrace
- Breakfast
US $146/Night
For 7 Nights US $1,021
10.0
Exceptional
(69 Reviews)
700 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $216/Night
For 7 Nights US $1,512
10.0
Exceptional
(2 Reviews)
1797.57 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Parking
US $687/Night
For 7 Nights US $4,809
10.0
Exceptional
(15 Reviews)
1 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $277/Night
For 7 Nights US $1,942
10.0
Exceptional
(10 Reviews)
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $473/Night
For 7 Nights US $3,310
10.0
Exceptional
(10 Reviews)
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $281/Night
For 7 Nights US $1,968
10.0
Exceptional
(10 Reviews)
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $206/Night
For 7 Nights US $1,442
Luxury Places to Stay in Windham
Over 426+ Luxury Places to Stay in or Near Windham
New
10763.91 ft²
33 Guests
12 Bedrooms
10 Bathrooms
House
- Fireplace/Heating
- Parking
- Internet
US $4,930/Night
For 7 Nights US $34,512
10.0
Exceptional
(9 Reviews)
11000 ft²
22 Guests
5 Bedrooms
7 Bathrooms
Family Friendly
House
- Hot Tub
- Skiing
- Fireplace/Heating
US $4,173/Night
For 7 Nights US $29,211
10.0
Exceptional
(25 Reviews)
10611 ft²
18 Guests
9 Bedrooms
7 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $3,780/Night
For 7 Nights US $26,460
10.0
Exceptional
(1 Review)
12 Guests
7 Bedrooms
7 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $3,380/Night
For 7 Nights US $23,663
10.0
Exceptional
(1 Review)
16 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $3,249/Night
For 7 Nights US $22,740
New
721.18 ft²
22 Guests
8 Bedrooms
6 Bathrooms
House
- Skiing
- Balcony/Terrace
- Parking
US $2,531/Night
For 7 Nights US $17,719
9.8
Exceptional
(9 Reviews)
7000 ft²
14 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Spa
US $2,310/Night
For 7 Nights US $16,171
9.8
Exceptional
(37 Reviews)
6600 ft²
24 Guests
8 Bedrooms
6 Bathrooms
Family Friendly
Ski Chalet
- Private Pool
- Hot Tub
- Fireplace/Heating
US $2,089/Night
For 7 Nights US $14,626
New
6490.64 ft²
20 Guests
8 Bedrooms
6 Bathrooms
Free Cancellation
House
- Skiing
- Fireplace/Heating
- Pet Friendly
US $1,844/Night
For 7 Nights US $12,908
Top-Rated Vacation Rentals with a Pool in Windham
Over 76+ Top-Rated Vacation Rentals with a Pool in or Near Windham
10.0
Exceptional
(170 Reviews)
4000 ft²
30 Guests
9 Bedrooms
5 Bathrooms
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Pool
US $1,748/Night
For 7 Nights US $12,236
10.0
Exceptional
(28 Reviews)
12 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
US $1,349/Night
For 7 Nights US $9,440
10.0
Exceptional
(24 Reviews)
1812 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $751/Night
For 7 Nights US $5,254
10.0
Exceptional
(16 Reviews)
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $497/Night
For 7 Nights US $3,479
10.0
Exceptional
(15 Reviews)
1812 ft²
12 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $890/Night
For 7 Nights US $6,230
10.0
Exceptional
(14 Reviews)
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $479/Night
For 7 Nights US $3,355
10.0
Exceptional
(12 Reviews)
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $1,591/Night
For 7 Nights US $11,140
10.0
Exceptional
(12 Reviews)
3500 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
US $846/Night
For 7 Nights US $5,925
10.0
Exceptional
(11 Reviews)
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Skiing
- Fireplace/Heating
- Pool
US $438/Night
For 7 Nights US $3,068
Pet-Friendly Vacation Rentals in Windham
Over 167+ Pet-Friendly Vacation Rentals in or Near Windham
10.0
Exceptional
(8 Reviews)
5 Guests
1 Bedroom
1 Bathroom
Pet Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Pet Friendly
US $194/Night
For 7 Nights US $1,361
10.0
Exceptional
(1 Review)
1001.04 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Skiing
- Fireplace/Heating
US $549/Night
For 7 Nights US $3,845
New
2992 ft²
14 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $738/Night
For 7 Nights US $5,164
10.0
Exceptional
(7 Reviews)
1 ft²
4 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $119/Night
For 7 Nights US $832
10.0
Exceptional
(1 Review)
1097.92 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Pet Friendly
- Parking
- Internet
US $177/Night
For 7 Nights US $1,239
10.0
Exceptional
(6 Reviews)
1 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $202/Night
For 7 Nights US $1,411
10.0
Exceptional
(5 Reviews)
960 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $353/Night
For 7 Nights US $2,470
10.0
Exceptional
(2 Reviews)
1100 ft²
7 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $278/Night
For 7 Nights US $1,948
10.0
Exceptional
(1 Review)
7 Guests
2 Bedrooms
2 Bathrooms
Pet Friendly
Condo
- Fireplace/Heating
- Pet Friendly
- Child Friendly
US $234/Night
For 7 Nights US $1,635
Large Vacation Homes & Villas in Windham
Over 185+ Large Vacation Homes & Villas in or Near Windham
New
2300 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $451/Night
For 7 Nights US $3,158
10.0
Exceptional
(1 Review)
7879.18 ft²
11 Guests
1 Bedroom
2 Bathrooms
House
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $413/Night
For 7 Nights US $2,892
10.0
Exceptional
(110 Reviews)
4200 ft²
14 Guests
6 Bedrooms
3 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,116/Night
For 7 Nights US $7,812
9.8
Exceptional
(8 Reviews)
2002.09 ft²
11 Guests
4 Bedrooms
2 Bathrooms
Free Cancellation
Ski Chalet
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $410/Night
For 7 Nights US $2,873
10.0
Exceptional
(79 Reviews)
1600 ft²
10 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Skiing
- Fireplace/Heating
US $220/Night
For 7 Nights US $1,542
10.0
Exceptional
(62 Reviews)
2028 ft²
8 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $358/Night
For 7 Nights US $2,509
10.0
Exceptional
(55 Reviews)
2900 ft²
12 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $740/Night
For 7 Nights US $5,179
10.0
Exceptional
(25 Reviews)
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $504/Night
For 7 Nights US $3,529
10.0
Exceptional
(23 Reviews)
4500 ft²
11 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
US $917/Night
For 7 Nights US $6,417
Wheelchair Accessible Vacation Homes in Windham
Over 20+ Wheelchair Accessible Vacation Homes in or Near Windham
10.0
Exceptional
(6 Reviews)
1727 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $630/Night
For 7 Nights US $4,412
4.2
Average
(11 Reviews)
28 Guests
8 Bedrooms
11 Bathrooms
Bed & Breakfast
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $206/Night
For 7 Nights US $1,442
8.8
Fabulous
(96 Reviews)
1 Bathroom
Family Friendly
Hotel
- Skiing
- Fireplace/Heating
- Pool
US $294/Night
For 7 Nights US $2,058
10.0
Exceptional
(2 Reviews)
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $1,491/Night
For 7 Nights US $10,435
New
4004.17 ft²
16 Guests
3 Bedrooms
3 Bathrooms
House
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $1,350/Night
For 7 Nights US $9,450
9.6
Exceptional
(13 Reviews)
1858 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $693/Night
For 7 Nights US $4,851
9.4
Exceptional
(8 Reviews)
1520 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Skiing
- Fireplace/Heating
- Pool
US $525/Night
For 7 Nights US $3,677
New
3000 ft²
8 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,335/Night
For 7 Nights US $9,342
10.0
Exceptional
(4 Reviews)
9 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Private Pool
- Hot Tub
- Skiing
US $450/Night
For 7 Nights US $3,150
Windham Resorts and Airbnb Homes Under $200
Over 35+ Windham Resorts and Airbnb Homes Under $200
10.0
Exceptional
(1 Review)
9 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $120/Night
For 7 Nights US $842
9.3
Exceptional
(20 Reviews)
226.05 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $149/Night
For 7 Nights US $1,043
9.6
Exceptional
(276 Reviews)
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Skiing
- Fireplace/Heating
- Pool
US $169/Night
For 7 Nights US $1,182
9.8
Exceptional
(50 Reviews)
975 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Skiing
- Fireplace/Heating
- Pool
US $181/Night
For 7 Nights US $1,269
8.7
Fabulous
(3 Reviews)
1216.32 ft²
8 Guests
3 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $189/Night
For 7 Nights US $1,323
9.6
Exceptional
(17 Reviews)
1100 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $172/Night
For 7 Nights US $1,202
9.6
Exceptional
(5 Reviews)
800 ft²
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $194/Night
For 7 Nights US $1,361
9.4
Exceptional
(10 Reviews)
1234 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Kitchen
- Parking
US $176/Night
For 7 Nights US $1,229
8.6
Fabulous
(4 Reviews)
900 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Balcony/Terrace
- Kitchen
- Parking
US $194/Night
For 7 Nights US $1,360
Instantly Bookable Vacation Homes in Windham
Over 186+ Instantly Bookable Vacation Homes in or Near Windham
10.0
Exceptional
(4 Reviews)
1400 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $207/Night
For 7 Nights US $1,447
10.0
Exceptional
(2 Reviews)
1200 ft²
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $254/Night
For 7 Nights US $1,777
10.0
Exceptional
(1 Review)
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
US $608/Night
For 7 Nights US $4,256
9.6
Exceptional
(63 Reviews)
1008 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $244/Night
For 7 Nights US $1,707
9.4
Exceptional
(8 Reviews)
900 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Balcony/Terrace
- Kitchen
- Internet
US $264/Night
For 7 Nights US $1,851
9.0
Exceptional
(59 Reviews)
1500 ft²
7 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $302/Night
For 7 Nights US $2,117
8.6
Fabulous
(4 Reviews)
2500 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $451/Night
For 7 Nights US $3,159
8.6
Fabulous
(4 Reviews)
900 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Condo
- Balcony/Terrace
- Kitchen
- Internet
US $249/Night
For 7 Nights US $1,743
8.0
Excellent
(2 Reviews)
250 ft²
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Cabin
- Pet Friendly
- Child Friendly
- Laundry
US $353/Night
For 7 Nights US $2,468
Book a Last Minute Place to Stay in Windham
About Windham Vacation Rentals
Explore over 435 vacation rentals in Windham with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Windham for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Windham. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Windham tailored to your preferences. On average, these rentals offer 1509.25 ft² of space, and are priced at an average of US $723 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Windham at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Windham
| Type | Count |
|---|---|
| Vacation Homes | 265 |
| Cabin Rentals | 41 |
| Ski Chalet Rentals | 29 |
| Holiday Apartments | 21 |
| Villas | 7 |
| Others | 6 |
| B&B | 5 |
| Cottages | 3 |
| Unique Vacation Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Windham
★ Pro Tip: Discover Your Ideal Vacation Rental in Windham with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Windham, NY
View the weather forecast for Windham before booking your Windham Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Windham, NY
Sunski offers a large selection of top attractions around Windham . Research things to do on your vacation before you visit Windham.
Other Places to Stay in Windham, NY
Frequently Asked Questions About Windham?
What are the top vacation rentals in Windham?
When organizing your trip to Windham, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Windham. Peruse our collection of highly-rated properties and secure your reservation today.
- Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
- Charming Mountain Retreat Lg Mod/Kit on Stream/Fire-pit/Hot Tub
- Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
- Cozy Caboose in the city
- Walk to slopes at Windham! Great ski home for families. Golf, bike, & hike too.
- Cutest Cabin in Windham close to ski slope and ski town
- Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!
- *GUT RENO 4 Season Nirvana*Hot Tub*WiFi*Fire Pit*Fireplace*Windhm Mtn View*2BBQs
- Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace
- Windham Family Getaway
How many vacation rentals have private pools in Windham?
Uncover 14 vacation rentals boasting private pools near Windham. Explore top-rated RBO homes offering access to a swimming pool:
- Majestic Villa in Windham - XL Pool, Movie Room, Hot tub, 6 Bedrooms, Gardens
- Lux Windham Getaway - Views & Indoor Heated Pool
- Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. Pizza Oven
- Custom Windham Mtn Villa with Pool, Theater and Views!
Which vacation homes or resorts in Windham are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Windham. Enjoy great views, locations and save money with SunSki Resorts.™
- Cozy Family-Friendly Townhouse Steps from Windham Mountain Resort - Unit 33
- Windham Ridge Chalet
- Beds on Clouds
How many SunSkiResorts vacation rentals or resorts are available in Windham?
Discover the ideal vacation rental in Windham with SunSki Resorts™. We provide an extensive selection of over 435 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Windham.
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