Windham Holiday Rentals
Apartment
10.0Exceptional
(108 Reviews)
1 Bedroom
1 Bath
2 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $257/Night
7 Nights - US $1,796
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
1797.57 ft²
- Parking
Spa
Internet
Child Friendly
US $687/Night
7 Nights - US $4,809
Bed & Breakfast
9.0Exceptional
(133 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
Skiing- Balcony/Terrace
US $146/Night
7 Nights - US $1,021
Cabin
10.0Exceptional
(72 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $252/Night
7 Nights - US $1,761
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
1797.57 ft²
Oceanfront- Parking
Ocean View
View
US $290/Night
7 Nights - US $2,032
Cabin
10.0Exceptional
(16 Reviews)
1 Bedroom
1 Bath
5 Guests
Hot Tub- Air Conditioner
- Internet
Pet Friendly
US $219/Night
7 Nights - US $1,535
Apartment
10.0Exceptional
(15 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $467/Night
7 Nights - US $3,267
Condo
10.0Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Parking
Pool- Balcony/Terrace
- Kitchen
US $233/Night
7 Nights - US $1,633
Cabin
10.0Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
6 Guests
960 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $471/Night
7 Nights - US $3,300
Luxury Holiday Rentals in Windham
Over 421+ Luxury Holiday Rentals in or Near Windham
Hotel
7 Baths
373.66 ft²
- Parking
- Pet Friendly
- Child Friendly
Security/Safety
US $8,499/Night
7 Nights - US $59,494
House
12 Bedrooms
10 Baths
33 Guests
10763.91 ft²
- Parking
- Internet
- Child Friendly
Accessibility
US $4,930/Night
7 Nights - US $34,512
House
10.0Exceptional
(9 Reviews)
5 Bedrooms
7 Baths
22 Guests
11000 ft²
- Hot Tub
- Parking
- Skiing
- Balcony/Terrace
US $4,632/Night
7 Nights - US $32,426
House
10.0Exceptional
(1 Review)
7 Bedrooms
7 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $3,833/Night
7 Nights - US $26,833
Cabin
10.0Exceptional
(1 Review)
6 Bedrooms
6 Baths
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $3,659/Night
7 Nights - US $25,613
Ski Chalet
9.8Exceptional
(39 Reviews)
8 Bedrooms
6 Baths
24 Guests
6600 ft²
Private Pool- Hot Tub
- Pool
- Balcony/Terrace
US $2,718/Night
7 Nights - US $19,029
House
9.8Exceptional
(10 Reviews)
5 Bedrooms
6 Baths
14 Guests
7000 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,587/Night
7 Nights - US $18,106
House
8 Bedrooms
6 Baths
22 Guests
721.18 ft²
- Parking
- Skiing
- Balcony/Terrace
- Air Conditioner
US $2,531/Night
7 Nights - US $17,719
House
1 Bedroom
1 Bath
- Hot Tub
- Parking
- Pool
- Spa
US $2,159/Night
7 Nights - US $15,112
Top-Rated Holiday Rentals with a Pool in Windham
Over 74+ The Best Private Villas and Holiday Rentals in Windham with a Pool
Cabin
10.0Exceptional
(170 Reviews)
9 Bedrooms
5 Baths
30 Guests
4000 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $2,078/Night
7 Nights - US $14,545
Condo
10.0Exceptional
(24 Reviews)
4 Bedrooms
4 Baths
10 Guests
1812 ft²
- Hot Tub
- Parking
- Pool
- Skiing
US $814/Night
7 Nights - US $5,696
Condo
10.0Exceptional
(16 Reviews)
3 Bedrooms
3 Baths
12 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $684/Night
7 Nights - US $4,785
House
10.0Exceptional
(16 Reviews)
4 Bedrooms
3 Baths
12 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $662/Night
7 Nights - US $4,634
Condo
10.0Exceptional
(15 Reviews)
4 Bedrooms
4 Baths
12 Guests
1812 ft²
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,022/Night
7 Nights - US $7,153
House
10.0Exceptional
(12 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $1,974/Night
7 Nights - US $13,816
House
10.0Exceptional
(11 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Parking
- Pool
- Skiing
- Balcony/Terrace
US $318/Night
7 Nights - US $2,227
Condo
10.0Exceptional
(10 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Parking
- Pool
- Skiing
US $974/Night
7 Nights - US $6,815
Ski Chalet
10.0Exceptional
(9 Reviews)
4 Bedrooms
4 Baths
12 Guests
3213 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,884/Night
7 Nights - US $13,188
Pet-Friendly Holiday Rentals in Windham
Over 159+ Pet-Friendly Holiday Rentals in or Near Windham
House
10.0Exceptional
(7 Reviews)
1 Bedroom
1 Bath
4 Guests
1 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $158/Night
7 Nights - US $1,103
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1097.92 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $177/Night
7 Nights - US $1,239
House
4 Bedrooms
4 Baths
14 Guests
2992 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $738/Night
7 Nights - US $5,164
Apartment
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $245/Night
7 Nights - US $1,716
Ski Chalet
9.8Exceptional
(8 Reviews)
4 Bedrooms
2 Baths
11 Guests
2002.09 ft²
- Parking
- Skiing
- Balcony/Terrace
- Air Conditioner
US $410/Night
7 Nights - US $2,873
House
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
9 Guests
- Hot Tub
- Breakfast
- Parking
- Pool
US $362/Night
7 Nights - US $2,533
New
Apartment
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
7 Guests
1100 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $354/Night
7 Nights - US $2,476
House
10.0Exceptional
(1 Review)
1 Bedroom
6 Baths
16 Guests
6491 ft²
- Parking
- Skiing
- Kitchen
- Air Conditioner
US $1,703/Night
7 Nights - US $11,918
Condo
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
7 Guests
- Pet Friendly
- Child Friendly
Laundry
Bedding/Linens
US $304/Night
7 Nights - US $2,129
Large Holiday Rentals and Private Villas in Windham
Over 175+ Large Holiday Rentals and Private Villas in or Near Windham
Cabin
10.0Exceptional
(171 Reviews)
5 Bedrooms
3 Baths
10 Guests
2500 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $580/Night
7 Nights - US $4,062
House
9.3Exceptional
(20 Reviews)
6 Bedrooms
4 Baths
12 Guests
226.05 ft²
- Parking
- Skiing
- Balcony/Terrace
- View
US $149/Night
7 Nights - US $1,043
House
10.0Exceptional
(114 Reviews)
6 Bedrooms
3 Baths
14 Guests
4200 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $1,482/Night
7 Nights - US $10,376
House
9.0Exceptional
(1 Review)
5 Bedrooms
4 Baths
16 Guests
3304.52 ft²
- Private Pool
- Oceanfront
EV Charge Station- Parking
US $1,336/Night
7 Nights - US $9,350
House
10.0Exceptional
(63 Reviews)
5 Bedrooms
2 Baths
8 Guests
2028 ft²
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $460/Night
7 Nights - US $3,221
House
10.0Exceptional
(60 Reviews)
4 Bedrooms
3 Baths
12 Guests
3000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $785/Night
7 Nights - US $5,492
House
10.0Exceptional
(23 Reviews)
4 Bedrooms
3 Baths
11 Guests
4500 ft²
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $1,054/Night
7 Nights - US $7,376
House
10.0Exceptional
(16 Reviews)
8 Bedrooms
3 Baths
22 Guests
4000 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,093/Night
7 Nights - US $7,654
House
10.0Exceptional
(15 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $584/Night
7 Nights - US $4,086
Wheelchair Accessible Holiday Homes in Windham
Over 19+ Wheelchair Accessible Holiday Homes in or Near Windham
Condo
10.0Exceptional
(7 Reviews)
3 Bedrooms
3 Baths
8 Guests
1727 ft²
- Hot Tub
- Parking
- Pool
- Skiing
US $812/Night
7 Nights - US $5,685
House
3 Bedrooms
3 Baths
16 Guests
4004.17 ft²
- Breakfast
- Parking
- Skiing
- Balcony/Terrace
US $1,350/Night
7 Nights - US $9,450
Hotel
8.8Fabulous
(105 Reviews)
1 Bath
- Breakfast
- Parking
- Pool
- Skiing
US $302/Night
7 Nights - US $2,112
Condo
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Parking
- Pool
- Skiing
US $583/Night
7 Nights - US $4,082
Hotel
9.5Exceptional
(15 Reviews)
10 Baths
565.1 ft²
- Oceanfront
- EV Charge Station
- Parking
- Pool
US $199/Night
7 Nights - US $1,393
Condo
9.6Exceptional
(14 Reviews)
4 Bedrooms
4 Baths
10 Guests
1858 ft²
- Hot Tub
- Parking
- Pool
- Skiing
US $819/Night
7 Nights - US $5,730
Condo
9.4Exceptional
(8 Reviews)
3 Bedrooms
3 Baths
8 Guests
1520 ft²
- Parking
- Pool
- Skiing
- Balcony/Terrace
US $578/Night
7 Nights - US $4,047
House
6 Bedrooms
4 Baths
8 Guests
3000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $1,524/Night
7 Nights - US $10,669
House
10.0Exceptional
(26 Reviews)
12 Bedrooms
10 Baths
33 Guests
11000 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $4,443/Night
7 Nights - US $31,103
Windham Private Villas and Holiday Homes Under $200
Over 28+ Windham Private Villas and Holiday Homes Under $200
Cabin
9.4Exceptional
(16 Reviews)
1 Bedroom
1 Bath
5 Guests
800 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $188/Night
7 Nights - US $1,315
House
8.7Fabulous
(3 Reviews)
3 Bedrooms
3 Baths
8 Guests
1216.32 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $189/Night
7 Nights - US $1,323
Bed & Breakfast
9.6Exceptional
(284 Reviews)
1 Bedroom
1 Bath
- Parking
- Pool
- Skiing
- Balcony/Terrace
US $188/Night
7 Nights - US $1,314
Condo
1 Bedroom
1 Bath
4 Guests
450 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $160/Night
7 Nights - US $1,117
House
8.6Fabulous
(7 Reviews)
2 Bedrooms
2 Baths
6 Guests
1097.92 ft²
- Parking
- Spa
- Internet
- Child Friendly
US $136/Night
7 Nights - US $952
Cabin
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Air Conditioner
- Internet
- Pet Friendly
US $123/Night
7 Nights - US $858
New
Apartment
9.2Exceptional
(45 Reviews)
1 Bedroom
1 Bath
3 Guests
600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $146/Night
7 Nights - US $1,024
Condo
4.7Average
(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Kitchen
- Laundry
- Bedding/Linens
US $81/Night
7 Nights - US $567
House
4.7Average
(9 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Kitchen
- Child Friendly
- Laundry
- Bedding/Linens
US $200/Night
7 Nights - US $1,400
Instantly Bookable Holiday Homes in Windham
Over 179+ Instantly Bookable Holiday Homes in or Near Windham
Condo
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
8 Guests
1200 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $349/Night
7 Nights - US $2,446
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $678/Night
7 Nights - US $4,748
House
9.8Exceptional
(52 Reviews)
2 Bedrooms
2 Baths
8 Guests
975 ft²
- Parking
- Pool
- Skiing
- Balcony/Terrace
US $231/Night
7 Nights - US $1,614
House
9.6Exceptional
(63 Reviews)
2 Bedrooms
2 Baths
6 Guests
1008 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $246/Night
7 Nights - US $1,723
House
9.6Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $283/Night
7 Nights - US $1,978
Condo
9.4Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
1234 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $257/Night
7 Nights - US $1,797
Condo
9.4Exceptional
(8 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Balcony/Terrace
- Kitchen
- Internet
- Child Friendly
US $347/Night
7 Nights - US $2,432
House
9.0Exceptional
(62 Reviews)
2 Bedrooms
2 Baths
7 Guests
1500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $220/Night
7 Nights - US $1,542
Cabin
8.6Fabulous
(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
2500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $696/Night
7 Nights - US $4,874
Book a Last Minute Place to Stay in Windham
About Casai's Private Villas and Holiday Rentals in Windham
Discover more than 430 vacation rentals available in Windham. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windham.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windham, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windham. On average, places to stay near Windham offer 1439.53 ft², with nightly prices averaging US $766.
With Casai, finding and comparing holiday rentals in Windham is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Windham
| Type | Count |
|---|---|
| Vacation Homes | 265 |
| Holiday Apartments | 16 |
| Villas | 6 |
| Cottages | 2 |
Use these Quick Filters to Find a Holiday Rental in Windham
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Windham.
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
Casai 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 holiday rentals in Windham?
With numerous options available in Windham, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Windham:
- DREAM LOG CABIN 110 Acres/Hot Tub/5 Minutes to the slopes/pond/river/internet
- Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
- Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
- Cozy Caboose in the city
- Cutest Cabin in Windham on site miniature golfing with fire pit and BBQ
- 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
- 'The Mountain House:' Windham Retreat w/Hot Tub!
How many holiday rentals have private pools in Windham?
Discover a selection of holiday rentals with private pools near Windham with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Catskills - Windham Villa | 6BR, 4 BA, XL Pool, Hot Tub & Cinema, Gardens
- Custom Windham Mtn Villa w/Pool, Theater & Views!
- Mountain Chalet with Hot Tub & Pool
- Windham Private heated indoor pool.
Which holiday homes in Windham are best for families?
If you're searching for a family-friendly holiday home in Windham, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Windham:
- Cozy Family-Friendly Townhouse Steps from Windham Mountain Resort - Unit 33
- The Windham A
- Hotel Vienna
How many Casai.com holiday rentals are available in Windham?
As of 2026, Casai boasts over 430 properties listed in the Windham area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windham.
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