Windham Vacation Rentals & Ski-in/Ski-out Homes
10.0
Exceptional
(165 Reviews)
- Vermont
- Londonderry
- 6.64 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $184/Night
For 7 Nights US $1,285
10.0
Exceptional
(2 Reviews)
- Vermont
- Stratton and Bromley Ski Areas
- 11.06 mi to center
3261.46 ft²
8 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Hot Tub
- Skiing
- Fireplace/Heating
US $725/Night
For 7 Nights US $5,077
10.0
Exceptional
(2 Reviews)
- Vermont
- Londonderry
- 6.53 mi to center
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Internet
US $216/Night
For 7 Nights US $1,512
10.0
Exceptional
(12 Reviews)
- Vermont
- Londonderry
- 6.53 mi to center
922 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Skiing
- Fireplace/Heating
- Kitchen
US $314/Night
For 7 Nights US $2,196
10.0
Exceptional
(2 Reviews)
645.83 ft²
4 Guests
1 Bedroom
1 Bathroom
Apartment
- Skiing
- Fireplace/Heating
- Parking
US $154/Night
For 7 Nights US $1,078
10.0
Exceptional
(2 Reviews)
- Vermont
- Londonderry
- 6.53 mi to center
650 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Skiing
- Fireplace/Heating
- Kitchen
US $270/Night
For 7 Nights US $1,891
10.0
Exceptional
(2 Reviews)
- Vermont
- Londonderry
- 6.29 mi to center
1200 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $252/Night
For 7 Nights US $1,763
10.0
Exceptional
(1 Review)
- Vermont
- Stratton and Bromley Ski Areas
- 11.59 mi to center
3 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Kitchen
- Internet
- Child Friendly
US $447/Night
For 7 Nights US $3,128
8.6
Fabulous
(16 Reviews)
720 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $151/Night
For 7 Nights US $1,057
Luxury Places to Stay in Windham
Over 69+ Luxury Places to Stay in or Near Windham
New
- Vermont
- Londonderry
- 6.29 mi to center
4300 ft²
10 Guests
7 Bedrooms
3 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,478/Night
For 7 Nights US $10,349
9.2
Exceptional
(45 Reviews)
- Vermont
- Londonderry
- 6.39 mi to center
6144 ft²
15 Guests
8 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,140/Night
For 7 Nights US $7,977
10.0
Exceptional
(9 Reviews)
3500 ft²
15 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $988/Night
For 7 Nights US $6,919
10.0
Exceptional
(5 Reviews)
15 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $959/Night
For 7 Nights US $6,714
New
3498.27 ft²
15 Guests
4 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $883/Night
For 7 Nights US $6,183
New
2848 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $616/Night
For 7 Nights US $4,312
10.0
Exceptional
(6 Reviews)
- Vermont
- Stratton and Bromley Ski Areas
- 11.06 mi to center
3263 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $608/Night
For 7 Nights US $4,254
10.0
Exceptional
(8 Reviews)
- Vermont
- Londonderry
- 7.46 mi to center
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Ski Chalet
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $498/Night
For 7 Nights US $3,487
New
- Vermont
- Stratton and Bromley Ski Areas
- 11.37 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Ski Chalet
- Hot Tub
- Spa
- Fireplace/Heating
US $483/Night
For 7 Nights US $3,379
Top-Rated Vacation Rentals with a Pool in Windham
Over 7+ Top-Rated Vacation Rentals with a Pool in or Near Windham
8.2
Excellent
(693 Reviews)
- Vermont
- Londonderry
- 6.40 mi to center
1 Bathroom
Couples Retreat
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $118/Night
For 7 Nights US $823
7.8
Very Good
(138 Reviews)
- Vermont
- Londonderry
- 6.41 mi to center
247.57 ft²
3 Bathrooms
Free Cancellation
Hotel
- Oceanfront
- Skiing
- Fireplace/Heating
US $116/Night
For 7 Nights US $814
10.0
Exceptional
(57 Reviews)
- Vermont
- West Townshend
- 2.89 mi to center
30 Guests
11 Bedrooms
6 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Spa
US $2,978/Night
For 7 Nights US $20,844
10.0
Exceptional
(1 Review)
- Vermont
- Stratton and Bromley Ski Areas
- 11.15 mi to center
3253 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Spa
- Fireplace/Heating
US $384/Night
For 7 Nights US $2,688
9.2
Exceptional
(116 Reviews)
- Vermont
- Londonderry
- 6.33 mi to center
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Hot Tub
- Spa
- Fireplace/Heating
US $192/Night
For 7 Nights US $1,344
New
- Vermont
- Londonderry
- 6.06 mi to center
3900 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,198/Night
For 7 Nights US $8,385
New
- Vermont
- Londonderry
- 6.42 mi to center
600 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
US $117/Night
For 7 Nights US $816
Pet-Friendly Vacation Rentals in Windham
Over 19+ Pet-Friendly Vacation Rentals in or Near Windham
10.0
Exceptional
(45 Reviews)
- Vermont
- Londonderry
- 6.94 mi to center
1800 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Ski Chalet
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $224/Night
For 7 Nights US $1,566
10.0
Exceptional
(21 Reviews)
- Central Vermont- Killington
- Andover
- 3.71 mi to center
2400 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $414/Night
For 7 Nights US $2,901
10.0
Exceptional
(6 Reviews)
- Vermont
- Stratton and Bromley Ski Areas
- 11.43 mi to center
2500 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $397/Night
For 7 Nights US $2,778
10.0
Exceptional
(3 Reviews)
1200 ft²
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Ski Chalet
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $288/Night
For 7 Nights US $2,019
9.6
Exceptional
(5 Reviews)
- Vermont
- Londonderry
- 6.67 mi to center
12 Guests
4 Bedrooms
1 Bathroom
Family Friendly
House
- Hot Tub
- Skiing
- Fireplace/Heating
US $223/Night
For 7 Nights US $1,561
9.0
Exceptional
(4 Reviews)
- Vermont
- South Londonderry
- 2.27 mi to center
9 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $402/Night
For 7 Nights US $2,816
New
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $446/Night
For 7 Nights US $3,125
New
- Vermont
- Londonderry
- 6.37 mi to center
1912 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $352/Night
For 7 Nights US $2,464
9.8
Exceptional
(12 Reviews)
- Vermont
- Londonderry
- 6.53 mi to center
630 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Spa
- Skiing
US $109/Night
For 7 Nights US $763
Large Vacation Homes & Villas in Windham
Over 15+ Large Vacation Homes & Villas in or Near Windham
10.0
Exceptional
(5 Reviews)
- Vermont
- Londonderry
- 7.51 mi to center
2400 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $383/Night
For 7 Nights US $2,680
10.0
Exceptional
(2 Reviews)
- Vermont
- Stratton and Bromley Ski Areas
- 11.11 mi to center
2800 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $428/Night
For 7 Nights US $2,999
10.0
Exceptional
(29 Reviews)
- Vermont
- South Londonderry
- 2.23 mi to center
3000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $385/Night
For 7 Nights US $2,692
10.0
Exceptional
(21 Reviews)
- Vermont
- Londonderry
- 7.38 mi to center
3431 ft²
8 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $597/Night
For 7 Nights US $4,181
10.0
Exceptional
(11 Reviews)
- Vermont
- Londonderry
- 6.41 mi to center
12 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Skiing
- Fireplace/Heating
- Pet Friendly
US $689/Night
For 7 Nights US $4,825
10.0
Exceptional
(4 Reviews)
2900 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $322/Night
For 7 Nights US $2,254
New
1500 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $531/Night
For 7 Nights US $3,716
New
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $508/Night
For 7 Nights US $3,554
5.0
Average
(4 Reviews)
- Vermont
- Londonderry
- 6.39 mi to center
2800 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Kitchen
- Child Friendly
- Laundry
US $457/Night
For 7 Nights US $3,199
Wheelchair Accessible Vacation Homes in Windham
Over 3+ Wheelchair Accessible Vacation Homes in or Near Windham
9.6
Exceptional
(7 Reviews)
- Vermont
- Londonderry
- 6.64 mi to center
1560 ft²
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Ski Chalet
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $259/Night
For 7 Nights US $1,815
9.2
Exceptional
(13 Reviews)
721.18 ft²
5 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Skiing
- Fireplace/Heating
- Kitchen
US $207/Night
For 7 Nights US $1,446
New
- Vermont
- West Townshend
- 1.64 mi to center
8 Guests
4 Bedrooms
5 Bathrooms
Family Friendly
House
- Kitchen
- Internet
- Child Friendly
US $449/Night
For 7 Nights US $3,143
Windham Resorts and Airbnb Homes Under $200
Over 7+ Windham Resorts and Airbnb Homes Under $200
10.0
Exceptional
(13 Reviews)
- Vermont
- Londonderry
- 6.53 mi to center
650 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Spa
- Skiing
- Fireplace/Heating
US $147/Night
For 7 Nights US $1,029
10.0
Exceptional
(11 Reviews)
- Vermont
- Londonderry
- 6.51 mi to center
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Skiing
- Kitchen
- Internet
US $160/Night
For 7 Nights US $1,120
4.7
Average
(3 Reviews)
- Vermont
- Londonderry
- 6.28 mi to center
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Ski Chalet
- Kitchen
- Air Conditioner
- Internet
US $109/Night
For 7 Nights US $763
3.6
Average
(7 Reviews)
1600 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $114/Night
For 7 Nights US $798
3.0
Average
(2 Reviews)
- Vermont
- Londonderry
- 6.37 mi to center
1800 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $163/Night
For 7 Nights US $1,141
3.0
Average
(1 Review)
- Vermont
- Londonderry
- 6.25 mi to center
800 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Kitchen
- Internet
- Laundry
US $137/Night
For 7 Nights US $959
New
- Vermont
- Londonderry
- 6.33 mi to center
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Kitchen
- Child Friendly
- Laundry
US $180/Night
For 7 Nights US $1,260
Instantly Bookable Vacation Homes in Windham
Over 17+ Instantly Bookable Vacation Homes in or Near Windham
10.0
Exceptional
(18 Reviews)
- Vermont
- Londonderry
- 7.05 mi to center
1612 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $351/Night
For 7 Nights US $2,455
9.6
Exceptional
(24 Reviews)
- Vermont
- Stratton and Bromley Ski Areas
- 11.60 mi to center
1 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $246/Night
For 7 Nights US $1,725
8.6
Fabulous
(13 Reviews)
- Vermont
- Londonderry
- 6.36 mi to center
2000 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $447/Night
For 7 Nights US $3,129
8.0
Excellent
(3 Reviews)
- Vermont
- Londonderry
- 6.53 mi to center
5 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Spa
- Skiing
- Fireplace/Heating
US $213/Night
For 7 Nights US $1,489
10.0
Exceptional
(4 Reviews)
- Vermont
- Londonderry
- 6.54 mi to center
600 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Spa
- Skiing
- Fireplace/Heating
US $206/Night
For 7 Nights US $1,442
10.0
Exceptional
(2 Reviews)
- Vermont
- West Townshend
- 2.90 mi to center
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $312/Night
For 7 Nights US $2,184
10.0
Exceptional
(1 Review)
- Vermont
- Londonderry
- 6.39 mi to center
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $407/Night
For 7 Nights US $2,847
New
- Vermont
- Londonderry
- 6.37 mi to center
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $522/Night
For 7 Nights US $3,653
New
- Vermont
- Londonderry
- 6.39 mi to center
2800 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $438/Night
For 7 Nights US $3,063
Book a Last Minute Place to Stay in Windham
About Windham Vacation Rentals
Explore over 78 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 1289.34 ft² of space, and are priced at an average of US $447 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 | 41 |
| Ski Chalet Rentals | 12 |
| Cabin Rentals | 5 |
| Holiday Apartments | 4 |
| B&B | 1 |
| Cottages | 1 |
| Others | 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, 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
Sunski 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 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.
- Private secluded trout cabin- sleeps 2
- Mountain chalet
- Maple Season Basecamp: 3 mi to Magic, Paved Road Access
- 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
- 1830's Recently Renovated Rustic Farmhouse, Windham Vermont
- Play & Relax in Windham – Spacious Bedrooms, Hot Tub, Fire Pit & Basement Den
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.™
- 3+ -bdrm chalet with loft sleeps 2 - 10 min from Magic, 20 mins to Stratton.
- Londonderry Chalet with Deck, Fire Pit and Views!
- Cozy Chalet on Magic Mountain
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 78 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.
People Also Ask
Finding the best prices in Windham
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