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Best Resorts in Ashland

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Check prices for these dates

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
In one month
Oct 30 - Nov 1
In two months
Nov 27 - Nov 29
No exact matches found, but these alternatives could be just right

Recommended hotels in Ashland

A covered porch with outdoor seating, a staircase, and potted plants.

1. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (496 reviews)
"Great place to stay!"
United States
Eric
$81 nightly
The price is $89
Oct 5 - Oct 6
Total with taxes and fees
The Colonial Motel
A swimming pool with lounge chairs and potted plants.

2. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (181 reviews)
"For such a small motel surprisingly clean and cozy. I will recommend this place without any hesitation."
United States
Marika
$120 nightly
The price is $130
Oct 6 - Oct 7
Total with taxes and fees
Moore's Motel
A log cabin with a deck, outdoor seating, and a view of a forest.

3. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (879 reviews)
"Very nice property with very nice rooms and great staff. Would definitely recommend!"
United States
Paul
$151 nightly
The price is $163
Oct 5 - Oct 6
Total with taxes and fees
Hotel Vienna
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

4. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (365 reviews)
"Great place for a couple."
United States
Abdul
$144 nightly
The price is $155
Nov 1 - Nov 2
Total with taxes and fees
The Winwood Condominiums
A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

5. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (137 reviews)
"A fantastic stay!"
United States
David
$135 nightly
The price is $146
Oct 5 - Oct 6
Total with taxes and fees
Antique Rose Inn Windham
A river flowing through a forested area with rocks and autumn-colored trees.

6. Black Bear Lodge

Black Bear Lodge
2.5 star property
Prattsville
9.0 out of 10, Wonderful, (155 reviews)
"Perfect quiet little motel close to great hikes. Staff was courteous and had tons of information on things to do in the area."
United States
Gerald
$149 nightly
The price is $161
Oct 4 - Oct 5
Total with taxes and fees
Black Bear Lodge
A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

7. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
9.4 out of 10, Exceptional, (9 reviews)
"The staff was super friendly and helpful. Mel took great care of us at the bar and got us checked in smoothly. She was happy to help us with local shopping and events. We will definitely come back next year!!! :-)"
United States
James
$135 nightly
The price is $146
Oct 5 - Oct 6
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

8. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (120 reviews)
"The cabin was adorable, everything at Dandies was delicious and Jamie was extremely helpful"
United States
Sharon
$319 nightly
The price is $344
Oct 4 - Oct 5
Total with taxes and fees
Eastwind Windham
A large, two-story house with multiple porches and string lights.

9. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (288 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
$174 nightly
The price is $188
Oct 4 - Oct 5
Total with taxes and fees
Albergo Allegria Hotel
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

10. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,022 reviews)
"I have been there twice and have really enjoyed my stay both times"
United States
Shubhangi
$155 nightly
The price is $168
Nov 1 - Nov 2
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
A multi-story building with outdoor seating and a stone-paved patio.

11. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
2.0 star property
Hunter
9.2 out of 10, Wonderful, (432 reviews)
"Great stay, beautiful place"
United Kingdom
Ryan
$197 nightly
The price is $212
Nov 1 - Nov 2
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
A room with two beds, wooden headboards, a red accent wall, and wooden flooring.

12. SunView Motel

SunView Motel
2.5 star property
Tannersville
8.6 out of 10, Excellent, (621 reviews)
"Great hotel!"
United States
Victoria
$118 nightly
The price is $128
Oct 4 - Oct 5
Total with taxes and fees
SunView Motel
A bedroom with a large window, a bed, and a view of a forest.

13. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
7.8 out of 10, Good, (35 reviews)
"Easy check in, nice layout of the apt, comfortable bed, nice to have a kitchen. Nearby lots of restaurants and mountain access. "
United States
Erica
$355 nightly
The price is $383
Oct 14 - Oct 15
Total with taxes and fees
The Haüs Windham
A park with Adirondack chairs and a table, surrounded by trees.

14. Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
Maplecrest
9.4 out of 10, Exceptional, (303 reviews)
"Service and breakfast were very good"
United States
Daniel
$166 nightly
The price is $179
Oct 20 - Oct 21
Total with taxes and fees
Mountain Treasure B&B
A modern kitchen with a central island, a dining area with a sofa, and a large window with a view of the outdoors.

15. Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (315 reviews)
"nice room, nice kitchen, nice renovated rest room, plus picnic tables and grounds"
United States
Sarah
$125 nightly
The price is $140
Oct 5 - Oct 6
Total with taxes and fees
Starlite Motel
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

16. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (128 reviews)
"Wonderful stay"
United States
Yousung
$361 nightly
The price is $390
Oct 29 - Oct 30
Total with taxes and fees
Wylder Hotel Windham
A wooden interior with a central fireplace, benches, and a window offering a forest view.

17. Mountain house with Scandinavian BBQ hut and Hot tub

Mountain house with Scandinavian BBQ hut and Hot tub
Jewett
10.0 out of 10, Exceptional, (76 reviews)
"Beautiful home, comfortable bedding, great amenities, great communication with host, overall lovely property. We loved the jacuzzi, bbq hut & she shed. "
United States
Despina M.
$645 nightly
The price is $697
Oct 5 - Oct 6
Total with taxes and fees
Mountain house with Scandinavian BBQ hut and Hot tub
A two-story building with large windows and a storefront.

18. Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (45 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
$125 nightly
The price is $135
Nov 1 - Nov 2
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Front of property

19. Windham NY Escape

Windham NY Escape
3.0 star property
Hensonville
10.0 out of 10, Exceptional, (1 review)
"The best "
United States
Miguel
$502 nightly
The price is $542
Oct 5 - Oct 6
Total with taxes and fees
Windham NY Escape
A building facade with a dark exterior, a window with blinds, a small porch with a railing, and flower planters on the porch.

20. Catskill Seasons Inn

Catskill Seasons Inn
2.5 star property
Shandaken
8.0 out of 10, Very good, (272 reviews)
""Catskill Seasons Inn provides amenities like free continental breakfast and a garden." There was not, in fact, breakfast provided (this is only on the weekends, a minor detail but very important if you are staying on a weekday)"
United States
Severn
$185 nightly
The price is $207
Oct 27 - Oct 28
Total with taxes and fees
Catskill Seasons 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.
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Top Ashland Hotel Reviews

Starlite Motel

Starlite Motel

10/10 Excellent
"Cute motel! Had updated bathroom. Also, had a kitchen with full refrigerator. Unfortunately, because of the rain we did not get to experience the grill, picnic area and fire pit out back. Location is great if you want to do some heavy duty hiking....lots of hikes/trailheads within 30 minutes of Starlite. Michelle reached out prior to our arrival with very helpful information. My only complaint was that the beds were a little too soft for me....had foam topper. I highly recommend the Phoenicia Diner (15 min away), Woodstock Brewery (15 min away...has good food, too) and Peekamoose (2 min away)."
Lisa 2-night trip
Posted 17 hours ago
Starlite Motel

Find out more about Ashland

Ashland Resorts information

Number of reviews
3,090
Accommodation
0 Resorts
Lowest Price
$89
Highest Price
$697

Frequently asked questions

What is Ashland like for a resort vacation?
You deserve a break, and a resort is the perfect place to pamper yourself with the services and amenities you need for a relaxing time in Ashland. One of the comfortable resorts in the area might be just what you're searching for, whether you want an amazing pool, a state-of-the-art fitness center, or nightly entertainment options.
What can I do in Ashland?
Ashland Town Hall, Windham Vineyards and Winery, and Windham Mountain Resort are a few interesting places to visit nearby. Other attractions in the area include Windham Country Club and Hunter Mountain.
What's the seasonal weather like in Ashland?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 26°F. The snowiest months in Ashland are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.

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