Windham Holiday Rentals
House
- Vermont
- ·
- West Townshend
- 2.89 mi to center
10.0Exceptional
(57 Reviews)
11 Bedrooms
6 Baths
30 Guests
Private Pool
Hot Tub
Spa
Skiing
د.إ.10,935/Night
7 Nights - د.إ.76,550
House
- Vermont
- ·
- Stratton and Bromley Ski Areas
- 11.06 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
3 Baths
8 Guests
3261.46 ft²
- Hot Tub
- Skiing
Fireplace/Heating
Balcony/Terrace
د.إ.2,664/Night
7 Nights - د.إ.18,645
Apartment
- Vermont
- ·
- Londonderry
- 6.53 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Kitchen
Internet
Child Friendly
د.إ.793/Night
7 Nights - د.إ.5,553
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
د.إ.864/Night
7 Nights - د.إ.6,049
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
د.إ.1,356/Night
7 Nights - د.إ.9,493
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
د.إ.1,626/Night
7 Nights - د.إ.11,381
Cabin
- Vermont
- ·
- Londonderry
- 7.05 mi to center
10.0Exceptional
(18 Reviews)
3 Bedrooms
2 Baths
8 Guests
1612 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,288/Night
7 Nights - د.إ.9,016
Condo
- Vermont
- ·
- Londonderry
- 6.53 mi to center
10.0Exceptional
(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
922 ft²
- Skiing
- Fireplace/Heating
- Kitchen
- Parking
د.إ.1,152/Night
7 Nights - د.إ.8,065
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
د.إ.2,526/Night
7 Nights - د.إ.17,683
Luxury Holiday Rentals in Windham
Over 68+ Luxury Holiday Rentals in or Near Windham
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
د.إ.5,129/Night
7 Nights - د.إ.35,906
House
10.0Exceptional
(9 Reviews)
4 Bedrooms
3 Baths
15 Guests
3500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.3,731/Night
7 Nights - د.إ.26,115
House
10.0Exceptional
(5 Reviews)
5 Bedrooms
4 Baths
15 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
د.إ.3,338/Night
7 Nights - د.إ.23,364
House
4 Bedrooms
3 Baths
15 Guests
3498.27 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Kitchen
د.إ.3,183/Night
7 Nights - د.إ.22,281
House
- Vermont
- ·
- Londonderry
- 6.29 mi to center
7 Bedrooms
3 Baths
10 Guests
4300 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
- View
د.إ.2,220/Night
7 Nights - د.إ.15,542
House
5 Bedrooms
3 Baths
10 Guests
2848 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,861/Night
7 Nights - د.إ.13,023
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
د.إ.1,777/Night
7 Nights - د.إ.12,439
House
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
Air Conditioner
د.إ.1,750/Night
7 Nights - د.إ.12,251
Ski Chalet
- Vermont
- ·
- Londonderry
- 7.46 mi to center
10.0Exceptional
(8 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Spa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
د.إ.1,646/Night
7 Nights - د.إ.11,524
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
د.إ.1,455/Night
7 Nights - د.إ.10,184
Bed & Breakfast
- Vermont
- ·
- Londonderry
- 6.33 mi to center
9.2Exceptional
(118 Reviews)
1 Bedroom
1 Bath
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
د.إ.590/Night
7 Nights - د.إ.4,128
Hotel
- Vermont
- ·
- Londonderry
- 6.40 mi to center
8.2Excellent
(700 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
د.إ.453/Night
7 Nights - د.إ.3,173
Hotel
- Vermont
- ·
- Londonderry
- 6.41 mi to center
7.8Very Good
(139 Reviews)
3 Baths
247.57 ft²
Oceanfront- Skiing
- Fireplace/Heating
- Pool
د.إ.427/Night
7 Nights - د.إ.2,989
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
د.إ.1,410/Night
7 Nights - د.إ.9,872
House
- Vermont
- ·
- Londonderry
- 6.06 mi to center
4 Bedrooms
3 Baths
8 Guests
3900 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
د.إ.4,399/Night
7 Nights - د.إ.30,794
Condo
- Vermont
- ·
- Londonderry
- 6.42 mi to center
1 Bedroom
1 Bath
2 Guests
600 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Kitchen
د.إ.428/Night
7 Nights - د.إ.2,997
Pet-Friendly Holiday Rentals in Windham
Over 16+ Pet-Friendly Holiday Rentals in or Near Windham
Ski Chalet
10.0Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
8 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,088/Night
7 Nights - د.إ.7,617
Cabin
- Vermont
- ·
- Londonderry
- 6.64 mi to center
10.0Exceptional
(165 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.839/Night
7 Nights - د.إ.5,872
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
د.إ.863/Night
7 Nights - د.إ.6,041
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
د.إ.1,388/Night
7 Nights - د.إ.9,717
House
- Vermont
- ·
- Londonderry
- 6.37 mi to center
3 Bedrooms
2 Baths
8 Guests
1912 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,326/Night
7 Nights - د.إ.9,280
House
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
7 Guests
1195 ft²
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Pet Friendly
د.إ.1,266/Night
7 Nights - د.إ.8,865
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
د.إ.400/Night
7 Nights - د.إ.2,802
House
3.6Average
(7 Reviews)
3 Bedrooms
2 Baths
7 Guests
1600 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Internet
د.إ.419/Night
7 Nights - د.إ.2,931
House
4 Bedrooms
3 Baths
10 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
د.إ.1,949/Night
7 Nights - د.إ.13,647
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
د.إ.1,494/Night
7 Nights - د.إ.10,459
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
د.إ.1,563/Night
7 Nights - د.إ.10,940
Cabin
10.0Exceptional
(4 Reviews)
4 Bedrooms
3 Baths
12 Guests
2900 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.1,183/Night
7 Nights - د.إ.8,278
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
د.إ.599/Night
7 Nights - د.إ.4,190
House
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
د.إ.1,865/Night
7 Nights - د.إ.13,052
House
- Vermont
- ·
- Londonderry
- 6.23 mi to center
4 Bedrooms
3 Baths
18 Guests
3800 ft²
- Pet Friendly
- Kitchen
- Air Conditioner
- Internet
د.إ.1,587/Night
7 Nights - د.إ.11,106
Ski Chalet
- Vermont
- ·
- Londonderry
- 6.47 mi to center
5 Bedrooms
3 Baths
14 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Balcony/Terrace
د.إ.1,280/Night
7 Nights - د.إ.8,961
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
د.إ.1,412/Night
7 Nights - د.إ.9,886
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
د.إ.2,194/Night
7 Nights - د.إ.15,355
Wheelchair Accessible Holiday Homes in Windham
Over 3+ 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
د.إ.1,126/Night
7 Nights - د.إ.7,885
House
9.2Exceptional
(13 Reviews)
1 Bedroom
1 Bath
5 Guests
721.18 ft²
- Skiing
- Fireplace/Heating
- Kitchen
- Child Friendly
د.إ.759/Night
7 Nights - د.إ.5,310
House
- Vermont
- ·
- West Townshend
- 1.64 mi to center
4 Bedrooms
5 Baths
8 Guests
- Kitchen
- Internet
- Child Friendly
Wheelchair Accessible
د.إ.1,649/Night
7 Nights - د.إ.11,543
Windham Private Villas and Holiday Homes Under $200
Over 7+ Windham Private Villas and Holiday Homes Under $200
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
د.إ.602/Night
7 Nights - د.إ.4,212
House
- Vermont
- ·
- Londonderry
- 6.53 mi to center
1 Bedroom
1 Bath
4 Guests
645.83 ft²
- Skiing
- Fireplace/Heating
- Parking
- Internet
د.إ.566/Night
7 Nights - د.إ.3,959
House
8.6Fabulous
(16 Reviews)
2 Bedrooms
1 Bath
5 Guests
720 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
د.إ.665/Night
7 Nights - د.إ.4,653
Condo
- Vermont
- ·
- Londonderry
- 6.51 mi to center
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
6 Guests
- Skiing
- Kitchen
- Internet
- Child Friendly
د.إ.588/Night
7 Nights - د.إ.4,113
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
د.إ.400/Night
7 Nights - د.إ.2,802
Condo
- Vermont
- ·
- Londonderry
- 6.25 mi to center
3.0Average
(1 Review)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Kitchen
- Internet
Laundry
TV
د.إ.503/Night
7 Nights - د.إ.3,522
Condo
- Vermont
- ·
- Londonderry
- 6.33 mi to center
1 Bedroom
1 Bath
4 Guests
- Kitchen
- Child Friendly
- Laundry
- TV
د.إ.661/Night
7 Nights - د.إ.4,627
Instantly Bookable Holiday Homes in Windham
Over 16+ Instantly Bookable Holiday Homes in or Near Windham
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
د.إ.992/Night
7 Nights - د.إ.6,945
Cottage
- 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
د.إ.838/Night
7 Nights - د.إ.5,861
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
د.إ.1,645/Night
7 Nights - د.إ.11,517
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
د.إ.905/Night
7 Nights - د.إ.6,335
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
د.إ.1,642/Night
7 Nights - د.إ.11,491
Apartment
- Vermont
- ·
- Londonderry
- 6.53 mi to center
8.0Excellent
(3 Reviews)
1 Bedroom
1 Bath
5 Guests
- Spa
- Skiing
- Fireplace/Heating
- Kitchen
د.إ.835/Night
7 Nights - د.إ.5,843
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
د.إ.757/Night
7 Nights - د.إ.5,296
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
د.إ.1,146/Night
7 Nights - د.إ.8,021
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
د.إ.1,494/Night
7 Nights - د.إ.10,456
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 1280.08 ft², with nightly prices averaging د.إ.1,608.
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 | 42 |
| Holiday Apartments | 2 |
| Cottages | 1 |
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
- 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
- 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:
- 3+ -bdrm house with loft - 10 min to Magic - 20 mins to Stratton - private area
- Cozy Ski-In/Ski-Out Condo on Magic Mountain
- Derry Woods Cabin: family retreat near Lowell Lake
How many Casai.ae 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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