Windham Holiday Rentals
Cabin
- Vermont
- ·
- Londonderry
- 6.64 mi to center
10.0Exceptional
(168 Reviews)
1 Bedroom
1 Bath
2 Guests
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $241/Night
7 Nights - US $1,687
House
- Vermont
- ·
- Stratton and Bromley Ski Areas
- 11.06 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
3261.46 ft²
Hot Tub
Skiing- Fireplace/Heating
View
US $708/Night
7 Nights - US $4,956
Apartment
- Vermont
- ·
- Londonderry
- 6.53 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Kitchen
Internet
Child Friendly
US $216/Night
7 Nights - US $1,512
Condo
- Vermont
- ·
- Londonderry
- 6.53 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
6 Guests
922 ft²
- Skiing
- Fireplace/Heating
- Kitchen
Parking
US $314/Night
7 Nights - US $2,196
House
- Vermont
- ·
- Londonderry
- 7.05 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
8 Guests
1614.59 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
US $369/Night
7 Nights - US $2,585
House
- Vermont
- ·
- Londonderry
- 6.29 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $228/Night
7 Nights - US $1,595
Condo
- Vermont
- ·
- Londonderry
- 6.53 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
650 ft²
- Skiing
- Fireplace/Heating
- Kitchen
- Parking
US $199/Night
7 Nights - US $1,393
Condo
- Vermont
- ·
- Londonderry
- 6.53 mi to center
9.8Exceptional
(14 Reviews)
1 Bedroom
1 Bath
6 Guests
650 ft²
Spa- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $164/Night
7 Nights - US $1,147
House
8.6Fabulous
(16 Reviews)
2 Bedrooms
1 Bath
5 Guests
720 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $159/Night
7 Nights - US $1,114
Luxury Holiday Rentals in Windham
Over 68+ Luxury Holiday Rentals in or Near Windham
House
- Vermont
- ·
- West Townshend
- 2.89 mi to center
10.0Exceptional
(59 Reviews)
11 Bedrooms
6 Baths
30 Guests
Private Pool- Hot Tub
- Spa
- Skiing
US $2,996/Night
7 Nights - US $20,972
House
- Vermont
- ·
- Londonderry
- 6.39 mi to center
9.2Exceptional
(45 Reviews)
8 Bedrooms
4 Baths
15 Guests
6144 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,397/Night
7 Nights - US $9,777
House
10.0Exceptional
(9 Reviews)
4 Bedrooms
3 Baths
15 Guests
3500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,004/Night
7 Nights - US $7,025
House
10.0Exceptional
(5 Reviews)
5 Bedrooms
4 Baths
15 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $909/Night
7 Nights - US $6,362
House
4 Bedrooms
3 Baths
15 Guests
3498.27 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Kitchen
US $867/Night
7 Nights - US $6,067
House
- Vermont
- ·
- Stratton and Bromley Ski Areas
- 11.06 mi to center
10.0Exceptional
(6 Reviews)
4 Bedrooms
3 Baths
8 Guests
3263 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $688/Night
7 Nights - US $4,815
House
- Vermont
- ·
- Londonderry
- 6.29 mi to center
7 Bedrooms
3 Baths
10 Guests
4300 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
US $605/Night
7 Nights - US $4,232
House
5 Bedrooms
3 Baths
10 Guests
2848 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $549/Night
7 Nights - US $3,845
House
- Vermont
- ·
- Londonderry
- 6.36 mi to center
3 Bedrooms
2 Baths
6 Guests
2002.09 ft²
- Spa
- Fireplace/Heating
- Parking
- Internet
US $479/Night
7 Nights - US $3,355
Top-Rated Holiday Rentals with a Pool in Windham
Over 7+ The Best Private Villas and Holiday Rentals in Windham with a Pool
House
- Vermont
- ·
- Stratton and Bromley Ski Areas
- 11.43 mi to center
10.0Exceptional
(6 Reviews)
3 Bedrooms
2 Baths
8 Guests
2500 ft²
- Private Pool
- Fireplace/Heating
Pool- Ocean View
US $406/Night
7 Nights - US $2,844
Bed & Breakfast
- Vermont
- ·
- Londonderry
- 6.33 mi to center
9.2Exceptional
(118 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $150/Night
7 Nights - US $1,049
Hotel
- Vermont
- ·
- Londonderry
- 6.40 mi to center
8.2Excellent
(700 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $123/Night
7 Nights - US $862
Hotel
- Vermont
- ·
- Londonderry
- 6.41 mi to center
7.8Very Good
(139 Reviews)
3 Baths
247.57 ft²
Oceanfront- Skiing
- Fireplace/Heating
- Pool
US $116/Night
7 Nights - US $814
House
- Vermont
- ·
- Stratton and Bromley Ski Areas
- 11.15 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
4 Baths
10 Guests
3253 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $384/Night
7 Nights - US $2,688
House
- Vermont
- ·
- Londonderry
- 6.06 mi to center
4 Bedrooms
3 Baths
8 Guests
3900 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,198/Night
7 Nights - US $8,385
Condo
- Vermont
- ·
- Londonderry
- 6.42 mi to center
1 Bedroom
1 Bath
2 Guests
600 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
US $117/Night
7 Nights - US $816
Pet-Friendly Holiday Rentals in Windham
Over 18+ Pet-Friendly Holiday Rentals in or Near Windham
Ski Chalet
- Vermont
- ·
- Londonderry
- 6.94 mi to center
10.0Exceptional
(45 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Skiing
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $233/Night
7 Nights - US $1,630
House
- Central Vermont- Killington
- ·
- Andover
- 3.71 mi to center
10.0Exceptional
(22 Reviews)
4 Bedrooms
2 Baths
10 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $470/Night
7 Nights - US $3,290
Ski Chalet
10.0Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
8 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $296/Night
7 Nights - US $2,074
House
- Vermont
- ·
- Londonderry
- 6.67 mi to center
9.6Exceptional
(5 Reviews)
4 Bedrooms
1 Bath
12 Guests
- Hot Tub
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $235/Night
7 Nights - US $1,645
House
- Vermont
- ·
- South Londonderry
- 2.27 mi to center
9.0Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $428/Night
7 Nights - US $2,994
House
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
Air Conditioner
US $477/Night
7 Nights - US $3,336
House
- Vermont
- ·
- Londonderry
- 6.37 mi to center
3 Bedrooms
2 Baths
8 Guests
1912 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $361/Night
7 Nights - US $2,527
Condo
- Vermont
- ·
- Londonderry
- 6.53 mi to center
9.8Exceptional
(12 Reviews)
1 Bedroom
1 Bath
6 Guests
630 ft²
- Hot Tub
- Spa
- Skiing
- Fireplace/Heating
US $109/Night
7 Nights - US $763
House
- Vermont
- ·
- Londonderry
- 6.41 mi to center
10.0Exceptional
(11 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Skiing
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $689/Night
7 Nights - US $4,825
Large Holiday Rentals and Private Villas in Windham
Over 14+ Large Holiday Rentals and Private Villas in or Near Windham
House
- Vermont
- ·
- Londonderry
- 7.51 mi to center
10.0Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $424/Night
7 Nights - US $2,966
House
- Vermont
- ·
- Stratton and Bromley Ski Areas
- 11.11 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
10 Guests
2800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $426/Night
7 Nights - US $2,979
House
- Vermont
- ·
- South Londonderry
- 2.23 mi to center
10.0Exceptional
(29 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $385/Night
7 Nights - US $2,692
House
- Vermont
- ·
- Londonderry
- 7.38 mi to center
10.0Exceptional
(21 Reviews)
5 Bedrooms
5 Baths
8 Guests
3431 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $597/Night
7 Nights - US $4,181
Cabin
10.0Exceptional
(4 Reviews)
4 Bedrooms
3 Baths
12 Guests
2900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $322/Night
7 Nights - US $2,254
House
4 Bedrooms
3 Baths
10 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $531/Night
7 Nights - US $3,716
House
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $508/Night
7 Nights - US $3,554
House
- Vermont
- ·
- Londonderry
- 6.39 mi to center
5.0Average
(4 Reviews)
5 Bedrooms
3 Baths
10 Guests
2800 ft²
- Kitchen
- Child Friendly
Laundry
TV
US $457/Night
7 Nights - US $3,199
House
- Vermont
- ·
- Londonderry
- 6.37 mi to center
3.0Average
(2 Reviews)
4 Bedrooms
2 Baths
12 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Internet
US $163/Night
7 Nights - US $1,141
Wheelchair Accessible Holiday Homes in Windham
Over 2+ Wheelchair Accessible Holiday Homes in or Near Windham
Ski Chalet
- Vermont
- ·
- Londonderry
- 6.64 mi to center
9.6Exceptional
(7 Reviews)
3 Bedrooms
1 Bath
8 Guests
1560 ft²
- Skiing
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $289/Night
7 Nights - US $2,021
House
- Vermont
- ·
- West Townshend
- 1.64 mi to center
4 Bedrooms
5 Baths
8 Guests
- Kitchen
- Internet
- Child Friendly
Wheelchair Accessible
US $449/Night
7 Nights - US $3,143
Windham Private Villas and Holiday Homes Under $200
Over 6+ Windham Private Villas and Holiday Homes Under $200
Condo
- Vermont
- ·
- Londonderry
- 6.51 mi to center
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
6 Guests
- Skiing
- Kitchen
- Internet
- Child Friendly
US $160/Night
7 Nights - US $1,120
House
- Vermont
- ·
- Londonderry
- 6.53 mi to center
1 Bedroom
1 Bath
4 Guests
645.83 ft²
- Skiing
- Fireplace/Heating
- Parking
- Internet
US $154/Night
7 Nights - US $1,078
Ski Chalet
- Vermont
- ·
- Londonderry
- 6.28 mi to center
4.7Average
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $109/Night
7 Nights - US $763
House
3.6Average
(7 Reviews)
3 Bedrooms
2 Baths
7 Guests
1600 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Internet
US $114/Night
7 Nights - US $798
Condo
- Vermont
- ·
- Londonderry
- 6.25 mi to center
3.0Average
(1 Review)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Kitchen
- Internet
- Laundry
- TV
US $137/Night
7 Nights - US $959
Condo
- Vermont
- ·
- Londonderry
- 6.33 mi to center
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Child Friendly
- Laundry
- TV
US $180/Night
7 Nights - US $1,260
Instantly Bookable Holiday Homes in Windham
Over 19+ Instantly Bookable Holiday Homes in or Near Windham
Cabin
- Vermont
- ·
- Londonderry
- 7.05 mi to center
10.0Exceptional
(22 Reviews)
3 Bedrooms
2 Baths
8 Guests
1612 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $369/Night
7 Nights - US $2,584
Apartment
- Vermont
- ·
- Londonderry
- 6.53 mi to center
8.0Excellent
(3 Reviews)
1 Bedroom
1 Bath
5 Guests
- Spa
- Skiing
- Fireplace/Heating
- Kitchen
US $235/Night
7 Nights - US $1,645
Condo
- Vermont
- ·
- Londonderry
- 6.54 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
6 Guests
600 ft²
- Spa
- Skiing
- Fireplace/Heating
- Kitchen
US $206/Night
7 Nights - US $1,442
Cabin
- Vermont
- ·
- Stratton and Bromley Ski Areas
- 11.59 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
3 Guests
- Kitchen
- Internet
- Child Friendly
Security/Safety
US $448/Night
7 Nights - US $3,136
Ski Chalet
- Vermont
- ·
- Stratton and Bromley Ski Areas
- 11.37 mi to center
1 Bedroom
1 Bath
2 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $484/Night
7 Nights - US $3,387
Cabin
- Vermont
- ·
- West Townshend
- 2.90 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $312/Night
7 Nights - US $2,184
House
- Vermont
- ·
- Londonderry
- 6.39 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $407/Night
7 Nights - US $2,847
House
- Vermont
- ·
- Stratton and Bromley Ski Areas
- 11.60 mi to center
9.6Exceptional
(24 Reviews)
3 Bedrooms
2 Baths
6 Guests
1 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $246/Night
7 Nights - US $1,725
House
- Vermont
- ·
- Londonderry
- 6.36 mi to center
8.6Fabulous
(13 Reviews)
3 Bedrooms
2 Baths
6 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $447/Night
7 Nights - US $3,129
Book a Last Minute Place to Stay in Windham
About Casai's Private Villas and Holiday Rentals in Windham
Discover more than 77 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 1285.81 ft², with nightly prices averaging US $441.
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 | 44 |
| Holiday Apartments | 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, VT
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, VT
Casai offers a large selection of top attractions around Windham . Research things to do on your vacation before you visit Windham.
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:
- Private secluded trout cabin- sleeps 2
- Luxury Two-Home Vermont Retreat Near Ski Resorts – Pool, Hot Tub & Sauna
- Mountain chalet
- Historic Vermont Farmhouse on 12 Acres, Quaint Vermont Experience
- Londonderry Chalet w/Deck, Fire Pit & Views!
- Cozy Ski-In/Ski-Out Condo on Magic Mountain
- New! Cozy, private Chalet with stunning Mountain Views.
- Tranquil Mountain Chalet- fireplace, deck, sauna, hiking trails, close to skiing
- Beautiful house w/mountain & pond views, hot tub, pool table, bbq, firepit, w/d
- Family-sized Farmhouse w/deck & access to private Vermont Quarry. Pet Friendly!
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:
- Tranquil Mountain Chalet- fireplace, deck, sauna, hiking trails, close to skiing
- Cozy Ski-In/Ski-Out Condo on Magic Mountain
- 3+ -bdrm house with loft - 10 min to Magic - 20 mins to Stratton - private area
How many Casai.nz holiday rentals are available in Windham?
As of 2026, Casai boasts over 77 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.
People Also Ask
Finding the best prices in Windham
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