Find hotels near Windsor Ski Lift, Ashland from CA $59

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jul 20 - Jul 21
Tomorrow
Jul 21 - Jul 22
Next weekend
Jul 25 - Jul 27
In two weeks
Aug 1 - Aug 3

Filter by

Guest rating
Guest rating
Star rating

Top Hotels Close to Windsor Ski Lift

Flagship Inn of Ashland
Desk, blackout drapes, iron/ironing board, WiFi

Flagship Inn of Ashland

2.5 star property
9.0 out of 10, Wonderful, (1009)
"Great stay!"
The price is CA $123
CA $137 total
includes taxes & fees
Jul 21 - Jul 22
Flagship Inn of Ashland
Callahan's Mountain Lodge
Panoramic Room, 1 King Bed, Jetted Tub, Mountain View | Terrace/patio

Callahan's Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (1154)
"We really enjoyed our stay!"
The price is CA $205
CA $209 total
includes taxes & fees
Jul 21 - Jul 22
Callahan's Mountain Lodge
Stratford Inn
Exterior detail

Stratford Inn

2.5 star property
9.4 out of 10, Exceptional, (1534)
"The perfect place to stay while visiting the,festival."
The price is CA $167
CA $186 total
includes taxes & fees
Jul 21 - Jul 22
Stratford Inn
Timbers INN and Suites
Exterior

Timbers INN and Suites

2.0 star property
8.6 out of 10, Excellent, (1002)
"Very nicely renovated - great location and great staff"
The price is CA $110
CA $123 total
includes taxes & fees
Aug 6 - Aug 7
Timbers INN and Suites
Holiday Inn Express & Suites Ashland by IHG
Exterior

Holiday Inn Express & Suites Ashland by IHG

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Would stay here again!"
The price is CA $199
CA $222 total
includes taxes & fees
Jul 28 - Jul 29
Holiday Inn Express & Suites Ashland by IHG
Ashland Hills Hotel & Suites
Lobby sitting area

Ashland Hills Hotel & Suites

3.0 star property
9.0 out of 10, Wonderful, (1470)
"Great place to stay, nice pool. "
The price is CA $190
CA $225 total
includes taxes & fees
Jul 22 - Jul 23
Ashland Hills Hotel & Suites
Relax Inn At Ashland
Standard Room, 1 King Bed (Newly Redone)

Relax Inn At Ashland

1.5 star property
6.8 out of 10, (459)
"Easy check in, friendly staff, clean."
The price is CA $98
CA $110 total
includes taxes & fees
Aug 19 - Aug 20
Relax Inn At Ashland
Oak Hill Bed & Breakfast
Coffee service

Oak Hill Bed & Breakfast

3.5 star property
9.8 out of 10, Exceptional, (63)
"We booked last minute..loved the room it was clean and comfy. The owners were fabulous and the breakfast was heavenly. "
The price is CA $340
CA $379 total
includes taxes & fees
Jul 21 - Jul 22
Oak Hill Bed & Breakfast
Country Willows Inn and Estate
Free daily full breakfast

Country Willows Inn and Estate

4.0 star property
9.8 out of 10, Exceptional, (26)
"A great place to stay!"
The price is CA $348
CA $353 total
includes taxes & fees
Jul 21 - Jul 22
Country Willows Inn and Estate
Best Western Windsor Inn
Exterior

Best Western Windsor Inn

2.5 star property
9.0 out of 10, Wonderful, (1006)
"very comfortable stay "
The price is CA $154
CA $172 total
includes taxes & fees
Aug 17 - Aug 18
Best Western Windsor Inn
The Peerless Hotel by WanderLodges
Honeymoon Suite #7, 1 Queen Bed, Jetted Tub, Mountain Views

The Peerless Hotel by WanderLodges

2.0 star property
9.6 out of 10, Exceptional, (78)
"The Peerless was so quiet and welcoming. Even though it was 100 degrees outside when I arrived, inside was wonderfully cool. I enjoyed the seating in the room and the bed was incredibly comfortable."
The price is CA $148
CA $240 total
includes taxes & fees
Jul 21 - Jul 22
The Peerless Hotel by WanderLodges
Ashland Springs Hotel
Garden

Ashland Springs Hotel

3.0 star property
9.4 out of 10, Exceptional, (1001)
"Great place to stay when attending a show at the OSF."
The price is CA $245
CA $280 total
includes taxes & fees
Aug 10 - Aug 11
Ashland Springs Hotel
Ashland Commons Hostel
Garden

Ashland Commons Hostel

2.0 star property
9.2 out of 10, Wonderful, (40)
"Another greet stay!"
The price is CA $59
CA $121 total
includes taxes & fees
Jul 21 - Jul 22
Ashland Commons Hostel
Winchester Inn
Bar (on property)

Winchester Inn

3.5 star property
9.6 out of 10, Exceptional, (248)
"Beautiful property, really comfortable bed, pillows and sheets! "
The price is CA $263
CA $311 total
includes taxes & fees
Jul 21 - Jul 22
Winchester Inn
Palm Cottages
Seasonal outdoor pool

Palm Cottages

2.5 star property
9.2 out of 10, Wonderful, (205)
"Great please with attractive grounds. Had a great vibe."
The price is CA $279
CA $311 total
includes taxes & fees
Jul 21 - Jul 22
Palm Cottages
Scottish Inn
Room, 2 Queen Beds, Non Smoking

Scottish Inn

2.5 star property
7.8 out of 10, Good, (659)
"This was a great average little hotel with a convenient location and an easy no frills place to stay. "
The price is CA $108
CA $121 total
includes taxes & fees
Aug 11 - Aug 12
Scottish Inn
Plaza Inn & Suites at Ashland Creek
Outdoor dining

Plaza Inn & Suites at Ashland Creek

3.0 star property
8.6 out of 10, Excellent, (1002)
"Very clean, quiet, great location, good breakfast"
The price is CA $221
CA $247 total
includes taxes & fees
Jul 21 - Jul 22
Plaza Inn & Suites at Ashland Creek
A Cowslip's Belle Inn
Main House | Terrace/patio

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (33)
"Terrific communication with owners, lovely property and close to downtown shops, theatre, etc. Highly recommend!"
The price is CA $267
CA $374 total
includes taxes & fees
Aug 6 - Aug 7
A Cowslip's Belle Inn
The Bard's Inn, BW Signature Collection by Best Western
Lobby

The Bard's Inn, BW Signature Collection by Best Western

2.5 star property
8.8 out of 10, Excellent, (1000)
"We loved the location, close to shops, parks and restaurants . Staff was friendly and our room had a nice patio. "
The price is CA $218
CA $243 total
includes taxes & fees
Jul 22 - Jul 23
The Bard's Inn, BW Signature Collection by Best Western
Abigail’s Bed & Breakfast Inn
Abigail Rockefeller

Abigail’s Bed & Breakfast Inn

3.5 star property
9.4 out of 10, Exceptional, (62)
"This is a great B&B. The proprietors go out of their way to think of every detail that will make your stay special. From the beautiful garden and comfortable room, to the daily complimentary fresh baked goods and the fantastic breakfast, during your stay you will feel pampered. The owners are also interesting and friendly if you want to engage. "
The price is CA $323
CA $360 total
includes taxes & fees
Jul 22 - Jul 23
Abigail’s Bed & Breakfast Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Windsor Ski Lift Hotel Reviews

Palm Cottages

Palm Cottages

10/10 Excellent
"A sweet little spot right downtown. Definitely a hidden gem. We enjoyed the outdoor salt water pool area and fountain. Loved the gardens and charming cottages. The bed was super comfy. The room (cottage) was quiet, nicely updated and clean. We will be back!!!!"
Stephanie 1-night trip
Posted 2 days ago
Palm Cottages

Frequently asked questions

What's the area like around Windsor Ski Lift?

Windsor Ski Lift is located in a family-friendly area of Ashland known for its picturesque gardens and array of dining options. Ashland is home to 322 hotels and other accommodations, so you can find something that's perfect for your stay.

Where is the best place to stay near Windsor Ski Lift?

Ashland Hills Hotel & Suites is one of the top choices for your stay based on our traveler data, and this hotel offers a restaurant and an outdoor pool. You'll find it 7.3 mi (11.8 km) from Windsor Ski Lift. Other good choices in the area include Callahan's Mountain Lodge and Flagship Inn of Ashland.

If I need to cancel the hotel reservation for my stay near Windsor Ski Lift, will I receive a refund?

Yes, most hotel bookings are fully refundable as long as you cancel before the hotel’s cancellation deadline, which is often 24 or 48 hours before your check-in date. If you have a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of booking. Plug in your dates, click on "Search", then you can use the "fully refundable" filter to get the top deals on offer near Windsor Ski Lift.

Where can I learn more about changing or cancelling my trip in the area near Windsor Ski Lift?

For more details about picking new dates or cancelling your stay near Windsor Ski Lift, click here.