Holiday rentals near Windsor Ski Lift
We found 354 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Windsor Ski Lift, scroll through and discover holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Windsor Ski Lift
Showing deals for:15 Aug - 22 Aug
Image gallery for Howell House-The Perfect Getaway
9.69.6 out of 10 rating
Exceptional
(11 reviews)
Howell House-The Perfect Getaway
Medford, OR
7% off
Price is AU$2,261
AU$2,261
AU$323 per night
includes taxes & fees
Image gallery for The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
1010 out of 10 rating
Exceptional
(43 reviews)
The Best In Ashland: Magnificent View, Privacy, Quality, Convenience, Very Clean
Ashland, OR
18% off
Price is AU$3,913
AU$3,913
AU$559 per night
includes taxes & fees
Image gallery for Charming Two Bedroom Private Cottage within walking distance to Ashland downtown
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Charming Two Bedroom Private Cottage within walking distance to Ashland downtown
Ashland, OR
8% off
Price is AU$4,157
AU$4,157
AU$594 per night
includes taxes & fees
Image gallery for Mountainside Chateau spectacular views and sunsets. 15 min to downtown Ashland!
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Mountainside Chateau spectacular views and sunsets. 15 min to downtown Ashland!
Ashland, OR
9% off
Price is AU$8,893
AU$8,893
AU$1,270 per night
includes taxes & fees
Image gallery for Quiet, Modern, Cottage
1010 out of 10 rating
Exceptional
(264 reviews)
Quiet, Modern, Cottage
Medford, OR
8% off
Price is AU$1,633
AU$1,633
AU$233 per night
includes taxes & fees
Image gallery for Tastefully remodeled 3 bedroom 2 bath home with large private back yard
1010 out of 10 rating
Exceptional
(39 reviews)
Tastefully remodeled 3 bedroom 2 bath home with large private back yard
Medford, OR
7% off
Price is AU$2,451
AU$2,451
AU$350 per night
includes taxes & fees
Image gallery for NEW Modern Luxury Downtown Talent - The Millie Haus
1010 out of 10 rating
Exceptional
(7 reviews)
NEW Modern Luxury Downtown Talent - The Millie Haus
Talent, OR
8% off
Price is AU$2,882
AU$2,882
AU$412 per night
includes taxes & fees
Image gallery for Gorgeous Lakeside HOUSE + Indoor SAUNA!
1010 out of 10 rating
Exceptional
(180 reviews)
Gorgeous Lakeside HOUSE + Indoor SAUNA!
Ashland, OR
18% off
Price is AU$2,802
AU$2,802
AU$400 per night
includes taxes & fees
Image gallery for Affordable Luxury- One block to Downtown
1010 out of 10 rating
Exceptional
(156 reviews)
Affordable Luxury- One block to Downtown
Ashland, Oregon
8% off
Price is AU$2,464
AU$2,464
AU$352 per night
includes taxes & fees
Image gallery for Large Private Carriage-House Retreat with Amazing Views
1010 out of 10 rating
Exceptional
(121 reviews)
Large Private Carriage-House Retreat with Amazing Views
Medford, OR
7% off
Price is AU$1,353
AU$1,353
AU$193 per night
includes taxes & fees
Image gallery for A Retreat From The City - The Little Farmhouse
1010 out of 10 rating
Exceptional
(59 reviews)
A Retreat From The City - The Little Farmhouse
Medford, OR
8% off
Price is AU$1,855
AU$1,855
AU$265 per night
includes taxes & fees
Image gallery for Beautiful Southern Charm awaits your visit
9.89.8 out of 10 rating
Exceptional
(60 reviews)
Beautiful Southern Charm awaits your visit
Medford, OR
7% off
Price is AU$1,774
AU$1,774
AU$253 per night
includes taxes & fees
Image gallery for Hyatt Prairie Mountain Cabin
9.69.6 out of 10 rating
Exceptional
(69 reviews)
Hyatt Prairie Mountain Cabin
Ashland, OR
8% off
Price is AU$3,342
AU$3,342
AU$477 per night
includes taxes & fees
Image gallery for Helman Street Penthouse with a View
1010 out of 10 rating
Exceptional
(28 reviews)
Helman Street Penthouse with a View
Ashland, OR
8% off
Price is AU$4,422
AU$4,422
AU$632 per night
includes taxes & fees
Image gallery for Serene Guest Cottage
1010 out of 10 rating
Exceptional
(14 reviews)
Serene Guest Cottage
Medford, OR
7% off
Price is AU$1,232
AU$1,232
AU$176 per night
includes taxes & fees
Image gallery for Three bedroom with king beds, 2 & a half bathroom. 2146 square foot house.
9.69.6 out of 10 rating
Exceptional
(39 reviews)
Three bedroom with king beds, 2 & a half bathroom. 2146 square foot house.
Medford, OR
7% off
Price is AU$2,354
AU$2,354
AU$336 per night
includes taxes & fees
Image gallery for Chateau Herbe ~ Oberon Suite w/ Kitchen
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Chateau Herbe ~ Oberon Suite w/ Kitchen
Ashland, OR
13% off
Price is AU$2,048
AU$2,048
AU$293 per night
includes taxes & fees
Image gallery for Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
1010 out of 10 rating
Exceptional
(38 reviews)
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Ashland, OR
15% off
Price is AU$3,303
AU$3,303
AU$472 per night
includes taxes & fees
Image gallery for Quiet and peaceful cottage close to downtown
9.89.8 out of 10 rating
Exceptional
(54 reviews)
Quiet and peaceful cottage close to downtown
Ashland, OR
16% off
Price is AU$2,149
AU$2,149
AU$307 per night
includes taxes & fees
Image gallery for Hyatt Lake Mountain Retreat
9.89.8 out of 10 rating
Exceptional
(76 reviews)
Hyatt Lake Mountain Retreat
Ashland, OR
8% off
Price is AU$2,231
AU$2,231
AU$319 per night
includes taxes & fees
Image gallery for Beautiful Guest Suite with Private Deck Overlooking Forest and Waterfall
9.89.8 out of 10 rating
Exceptional
(84 reviews)
Beautiful Guest Suite with Private Deck Overlooking Forest and Waterfall
Ashland, OR
8% off
Price is AU$1,769
AU$1,769
AU$253 per night
includes taxes & fees
Image gallery for Hyatt Prairie Mountain Cabin
1010 out of 10 rating
Exceptional
(52 reviews)
Hyatt Prairie Mountain Cabin
Ashland, OR
8% off
Price is AU$2,299
AU$2,299
AU$328 per night
includes taxes & fees
Image gallery for Chateau Herbe ~ Vienna Room
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Chateau Herbe ~ Vienna Room
Ashland, OR
13% off
Price is AU$1,726
AU$1,726
AU$247 per night
includes taxes & fees
Image gallery for The Dogwood Suite at Tudor House Vacation Rentals
9.49.4 out of 10 rating
Exceptional
(92 reviews)
The Dogwood Suite at Tudor House Vacation Rentals
Ashland, OR
13% off
Price is AU$2,172
AU$2,172
AU$310 per night
includes taxes & fees
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Find the best place to stay - Windsor Ski Lift
A Cowslip's Belle Inn
Sleeps 3 · 1 bedroom
9.89.8 out of 10
Exceptionalexceptional
31 reviews(31 reviews)
Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
38 reviews(38 reviews)
Railroad District, steps to downtown, everything you need to enjoy Ashland!
Sleeps 5 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
137 reviews(137 reviews)
In the historic railroad district, walking distance to all the best of Ashland!
Sleeps 8 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
178 reviews(178 reviews)
Ashland Lodge w/ Lake Views & Game Room Loft
Sleeps 13 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
68 reviews(68 reviews)
Downtown Ashland private cottage with garden patio
Sleeps 3 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value