72+ Vacation Home Rentals in Windsor |
Windsor Vacation Rentals & Ski-in/Ski-out Homes
10.0
Exceptional
(76 Reviews)
- Central Vermont- Killington
- Windsor
- 1.37 mi to center
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $229/Night
For 7 Nights US $1,605
10.0
Exceptional
(2 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.26 mi to center
1948.27 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Free Cancellation
House
- Fireplace/Heating
- Pet Friendly
- Parking
US $507/Night
For 7 Nights US $3,547
9.0
Exceptional
(823 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.27 mi to center
1 Bathroom
Family Friendly
Resort
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $168/Night
For 7 Nights US $1,173
10.0
Exceptional
(64 Reviews)
- Central Vermont- Killington
- Windsor
- 1.40 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $185/Night
For 7 Nights US $1,294
10.0
Exceptional
(1 Review)
- Central Vermont- Killington
- Windsor
- 1.73 mi to center
3465.98 ft²
9 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Parking
US $912/Night
For 7 Nights US $6,386
10.0
Exceptional
(4 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.27 mi to center
700 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $192/Night
For 7 Nights US $1,346
10.0
Exceptional
(3 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.03 mi to center
520 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $333/Night
For 7 Nights US $2,328
10.0
Exceptional
(1 Review)
- Central Vermont- Killington
- Brownsville
- 1.03 mi to center
520 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $343/Night
For 7 Nights US $2,399
10.0
Exceptional
(1 Review)
- Central Vermont- Killington
- Brownsville
- 1.03 mi to center
520 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $338/Night
For 7 Nights US $2,363
Luxury Places to Stay in Windsor
Over 63+ Luxury Places to Stay in or Near Windsor
New
- Central Vermont- Killington
- Windsor
- 2.40 mi to center
39 Guests
16 Bedrooms
19 Bathrooms
Group Friendly
House
- Internet
- Child Friendly
- Security/Safety
US $3,967/Night
For 7 Nights US $27,770
8.0
Excellent
(2 Reviews)
- Central Vermont- Killington
- Windsor
- 1.73 mi to center
3464 ft²
9 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $812/Night
For 7 Nights US $5,682
10.0
Exceptional
(1 Review)
- Central Vermont- Killington
- Brownsville
- 0.93 mi to center
8 Guests
5 Bedrooms
4 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
US $604/Night
For 7 Nights US $4,226
New
- Central Vermont- Killington
- Windsor
- 2.79 mi to center
1532 ft²
7 Guests
4 Bedrooms
2 Bathrooms
Cabin
- Fireplace/Heating
- Air Conditioner
- Internet
US $516/Night
For 7 Nights US $3,614
9.8
Exceptional
(42 Reviews)
- Central Vermont- Killington
- Windsor
- 1.87 mi to center
3000 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $487/Night
For 7 Nights US $3,410
10.0
Exceptional
(21 Reviews)
- Central Vermont- Killington
- Windsor
- 3.34 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $477/Night
For 7 Nights US $3,338
9.8
Exceptional
(98 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.15 mi to center
3000 ft²
14 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $444/Night
For 7 Nights US $3,107
New
- Central Vermont- Killington
- Brownsville
- 0.90 mi to center
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $426/Night
For 7 Nights US $2,981
New
- Central Vermont- Killington
- Windsor
- 2.55 mi to center
4 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Parking
- Air Conditioner
US $424/Night
For 7 Nights US $2,966
Top-Rated Vacation Rentals with a Pool in Windsor
Over 15+ Top-Rated Vacation Rentals with a Pool in or Near Windsor
10.0
Exceptional
(2 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.45 mi to center
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
US $252/Night
For 7 Nights US $1,763
9.6
Exceptional
(84 Reviews)
- Central Vermont- Killington
- Windsor
- 1.50 mi to center
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $210/Night
For 7 Nights US $1,471
9.6
Exceptional
(17 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.09 mi to center
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
US $286/Night
For 7 Nights US $2,000
9.6
Exceptional
(15 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.21 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
US $234/Night
For 7 Nights US $1,637
9.0
Exceptional
(2 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.01 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Villa
- Fireplace/Heating
- Pool
- Kitchen
US $199/Night
For 7 Nights US $1,396
8.8
Fabulous
(205 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.26 mi to center
991.82 ft²
47 Guests
7 Bathrooms
Family Friendly
Resort
- Private Pool
- Fireplace/Heating
- Pool
US $140/Night
For 7 Nights US $980
6.0
Good
(1 Review)
- Central Vermont- Killington
- Brownsville
- 1.27 mi to center
969 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $264/Night
For 7 Nights US $1,847
New
699.65 ft²
4 Guests
1 Bedroom
1 Bathroom
House
- Private Pool
- Hot Tub
- Spa
US $215/Night
For 7 Nights US $1,505
New
- Central Vermont- Killington
- Windsor
- 2.60 mi to center
2000 ft²
7 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Spa
- Fireplace/Heating
- Pool
US $579/Night
For 7 Nights US $4,053
Pet-Friendly Vacation Rentals in Windsor
Over 15+ Pet-Friendly Vacation Rentals in or Near Windsor
New
- Central Vermont- Killington
- Brownsville
- 1.03 mi to center
520 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $344/Night
For 7 Nights US $2,407
New
- Central Vermont- Killington
- Brownsville
- 1.03 mi to center
520 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $343/Night
For 7 Nights US $2,399
10.0
Exceptional
(16 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.26 mi to center
1950 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $420/Night
For 7 Nights US $2,937
10.0
Exceptional
(1 Review)
- Central Vermont- Killington
- Windsor
- 1.46 mi to center
8 Guests
4 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Internet
US $402/Night
For 7 Nights US $2,815
8.4
Excellent
(11 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.33 mi to center
1500 ft²
9 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Skiing
- Fireplace/Heating
- Balcony/Terrace
US $280/Night
For 7 Nights US $1,960
10.0
Exceptional
(2 Reviews)
- Central Vermont- Killington
- Brownsville
- 0.91 mi to center
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $297/Night
For 7 Nights US $2,078
10.0
Exceptional
(30 Reviews)
- Central Vermont- Killington
- Windsor
- 2.94 mi to center
8 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $379/Night
For 7 Nights US $2,650
9.6
Exceptional
(12 Reviews)
- Central Vermont- Killington
- Brownsville
- 1.33 mi to center
1350 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $346/Night
For 7 Nights US $2,422
New
- Central Vermont- Killington
- Brownsville
- 1.12 mi to center
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $658/Night
For 7 Nights US $4,605
Large Vacation Homes & Villas in Windsor
Over 5+ Large Vacation Homes & Villas in or Near Windsor
New
- Central Vermont- Killington
- Brownsville
- 1.54 mi to center
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $294/Night
For 7 Nights US $2,058
10.0
Exceptional
(1 Review)
- Central Vermont- Killington
- Windsor
- 2.48 mi to center
14500 ft²
32 Guests
15 Bedrooms
15 Bathrooms
Family Friendly
House
- Spa
- Fireplace/Heating
- Lake View
US $4,100/Night
For 7 Nights US $28,700
New
- Central Vermont- Killington
- Windsor
- 2.65 mi to center
7 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Air Conditioner
- Internet
- Child Friendly
US $525/Night
For 7 Nights US $3,675
9.8
Exceptional
(7 Reviews)
- Vermont
- Hartland Four Corners
- 1.16 mi to center
2000 ft²
10 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $383/Night
For 7 Nights US $2,681
New
- Central Vermont- Killington
- Brownsville
- 0.84 mi to center
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $798/Night
For 7 Nights US $5,585
Wheelchair Accessible Vacation Homes in Windsor
Over 3+ Wheelchair Accessible Vacation Homes in or Near Windsor
10.0
Exceptional
(1 Review)
- Central Vermont- Killington
- Brownsville
- 0.91 mi to center
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $296/Night
For 7 Nights US $2,073
New
- Central Vermont- Killington
- Brownsville
- 1.24 mi to center
969 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $470/Night
For 7 Nights US $3,287
New
- Central Vermont- Killington
- Brownsville
- 1.24 mi to center
699 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Condo
- Hot Tub
- Skiing
- Fireplace/Heating
US $389/Night
For 7 Nights US $2,720
Windsor Resorts and Airbnb Homes Under $200
Over 9+ Windsor Resorts and Airbnb Homes Under $200
New
- Central Vermont- Killington
- Brownsville
- 1.41 mi to center
4 Guests
1 Bathroom
Family Friendly
Resort
- Air Conditioner
- Internet
- Child Friendly
US $175/Night
For 7 Nights US $1,223
New
- Central Vermont- Killington
- Windsor
- 2.01 mi to center
4 Guests
1 Bathroom
Family Friendly
Resort
- Fireplace/Heating
- Air Conditioner
- Internet
US $151/Night
For 7 Nights US $1,058
New
- Central Vermont- Killington
- Brownsville
- 1.41 mi to center
4 Guests
1 Bathroom
Family Friendly
Resort
- Fireplace/Heating
- Pool
- Kitchen
US $131/Night
For 7 Nights US $918
New
- Central Vermont- Killington
- Brownsville
- 1.22 mi to center
4 Guests
1 Bathroom
Family Friendly
Resort
- Hot Tub
- Fireplace/Heating
- Pool
US $83/Night
For 7 Nights US $580
10.0
Exceptional
(1 Review)
- Central Vermont- Killington
- Brownsville
- 1.07 mi to center
8 Guests
2 Bathrooms
Group Friendly
Resort
- Fireplace/Heating
- Air Conditioner
- Internet
US $181/Night
For 7 Nights US $1,267
New
- Central Vermont- Killington
- Windsor
- 2.62 mi to center
1546 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Spa
- Pool
- Balcony/Terrace
US $119/Night
For 7 Nights US $833
New
- Central Vermont- Killington
- Brownsville
- 1.17 mi to center
4 Guests
1 Bathroom
Family Friendly
Resort
- Fireplace/Heating
- Air Conditioner
- Internet
US $123/Night
For 7 Nights US $862
New
- Central Vermont- Killington
- Brownsville
- 1.15 mi to center
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Breakfast
- Air Conditioner
US $117/Night
For 7 Nights US $818
New
- Central Vermont- Killington
- Brownsville
- 1.25 mi to center
4 Guests
1 Bathroom
Couples Retreat
Resort
- Fireplace/Heating
- Air Conditioner
- Internet
US $189/Night
For 7 Nights US $1,325
Instantly Bookable Vacation Homes in Windsor
Over 10+ Instantly Bookable Vacation Homes in or Near Windsor
10.0
Exceptional
(5 Reviews)
- Central Vermont- Killington
- Windsor
- 1.71 mi to center
2600 ft²
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $337/Night
For 7 Nights US $2,359
10.0
Exceptional
(8 Reviews)
376.74 ft²
2 Bathrooms
Hotel
- Balcony/Terrace
- Parking
- Air Conditioner
US $372/Night
For 7 Nights US $2,604
New
- Central Vermont- Killington
- Brownsville
- 1.33 mi to center
1000 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $274/Night
For 7 Nights US $1,915
New
- Central Vermont- Killington
- Brownsville
- 1.24 mi to center
6 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Fireplace/Heating
- Air Conditioner
US $258/Night
For 7 Nights US $1,803
New
- Central Vermont- Killington
- Brownsville
- 1.51 mi to center
4 Guests
1 Bathroom
Family Friendly
Resort
- Fireplace/Heating
- Air Conditioner
- Internet
US $206/Night
For 7 Nights US $1,443
10.0
Exceptional
(8 Reviews)
- Central Vermont- Killington
- Brownsville
- 2.02 mi to center
1200 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $350/Night
For 7 Nights US $2,450
New
- Central Vermont- Killington
- Brownsville
- 1.37 mi to center
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $528/Night
For 7 Nights US $3,696
New
- Central Vermont- Killington
- Brownsville
- 1.13 mi to center
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
Condo
- Hot Tub
- Spa
- Fireplace/Heating
US $225/Night
For 7 Nights US $1,575
New
- Central Vermont- Killington
- Brownsville
- 1.23 mi to center
6 Guests
2 Bathrooms
Family Friendly
Resort
- Hot Tub
- Fireplace/Heating
- Air Conditioner
US $308/Night
For 7 Nights US $2,156
Book a Last Minute Place to Stay in Windsor
About Windsor Vacation Rentals
Explore over 72 vacation rentals in Windsor 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 Windsor 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 Windsor. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Windsor tailored to your preferences. On average, these rentals offer 823.51 ft² of space, and are priced at an average of US $445 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Windsor 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 Windsor
| Type | Count |
|---|---|
| Vacation Homes | 25 |
| Cabin Rentals | 12 |
| Villas | 5 |
| Cottages | 2 |
| Holiday Apartments | 1 |
Use these Quick Filters to Find a Vacation Rental in Windsor
★ Pro Tip: Discover Your Ideal Vacation Rental in Windsor 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 Windsor, VT
View the weather forecast for Windsor before booking your Windsor 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 Windsor, VT
Sunski offers a large selection of top attractions around Windsor . Research things to do on your vacation before you visit Windsor.
Other Places to Stay in Windsor, VT
Frequently Asked Questions About Windsor?
What are the top vacation rentals in Windsor?
When organizing your trip to Windsor, 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 Windsor. Peruse our collection of highly-rated properties and secure your reservation today.
- Meadow View- 35 Acres outside your door
- Sunset Cabin - your private romantic hideaway
- Long Range Mountain Views in West Windsor
- Inviting Vermont Home On Mount Ascutney!
- Snapdragon Inn
- Antique farmhouse with spectacular mountain view in a bucolic setting.
- Enjoy snowball fights or romantic nights in a 1BD vacation apartment
- Scandi-Chic Luxury Loft Near Okemo With Solo Stove And EV Charger
- Inviting Vermont Home On Mount Ascutney!
- Villa Near Biking and Hiking Trails
Which vacation homes or resorts in Windsor are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Windsor. Enjoy great views, locations and save money with SunSki Resorts.™
- Lovely 2 Bedroom Townhouse on Ascutney Mountain
- Ascutney Retreat
- Lovely Vermont Cabin on a quiet street
How many SunSkiResorts vacation rentals or resorts are available in Windsor?
Discover the ideal vacation rental in Windsor with SunSki Resorts™. We provide an extensive selection of over 72 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Windsor.
People Also Ask
Finding the best prices in Windsor
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