Ashland Vacation Rentals

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Our top choices for Ashland vacation rentals

Starlite Motel

Starlite Motel
2.5 star property
Big Indian
9.2 out of 10, Wonderful, (275)
"Awesome place to stay!"
United States
Earl
$111 nightly
The price is $125
Jan 6 - Jan 7, 2026
Total with taxes and fees
Starlite Motel

Suites on Main

Suites on Main
3.0 star property
Margaretville
7.2 out of 10, Good, (78)
"Good place to stay and reasonable "
Canada
Marney
$144 nightly
The price is $158
Jan 4 - Jan 5, 2026
Total with taxes and fees
Suites on Main

Cozy Cabin-Catskills secluded Mountain retreat

Cozy Cabin-Catskills secluded Mountain retreat
2.0 star property
Gilboa
9.6 out of 10, Exceptional, (4)
"Great place to get away. "
United States
Joshua
$254 nightly
The price is $284
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy Cabin-Catskills secluded Mountain retreat

Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms

Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Windham
10.0 out of 10, Exceptional, (1)
"Great spacious property, inside and out. Great host, Communicative and organized. Special place."
United States
Bryan F.
$3,087 nightly
The price is $3,334
Jan 5 - Jan 6, 2026
Total with taxes and fees
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms

Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
10.0 out of 10, Exceptional, (3)
"Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer."
United States
Matthew M.
$164 nightly
The price is $173
Jan 4 - Jan 5, 2026
Total with taxes and fees
Jessie's Harvest House Suite

Cozy Waterfall Home | Close to All Mountains/Hikes

Cozy Waterfall Home | Close to All Mountains/Hikes
3.0 star property
East Durham
10.0 out of 10, Exceptional, (3)
"The host is very responsive and the listing is accurate about what to expect with the property."
United States
John K.
$298 nightly
The price is $322
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cozy Waterfall Home | Close to All Mountains/Hikes

Large Cook's Kitchen; 15 min to Belleayre Ski Center; 1st Fl Bedroom w/ Ensuite

Large Cook's Kitchen; 15 min to Belleayre Ski Center; 1st Fl Bedroom w/ Ensuite
2.0 star property
Halcott Center
10.0 out of 10, Exceptional, (1)
"Perfectly done! Kids loved it!!!!"
United States
Jasmina
$409 nightly
The price is $442
Jan 7 - Jan 8, 2026
Total with taxes and fees
Large Cook's Kitchen; 15 min to Belleayre Ski Center; 1st Fl Bedroom w/ Ensuite

Cozy Home, Wood-burning Fireplace, Ski Belleayre

Cozy Home, Wood-burning Fireplace, Ski Belleayre
Margaretville
9.8 out of 10, Exceptional, (10)
"Dunraven River House was perfect for our weekend away. The house was clean, comfortable and exactly as listed. The property so was peaceful and I loved having the sounds of the river right outside the door! We’d definitely stay again! "
United States
Angela P.
$315 nightly
The price is $347
Jan 12 - Jan 13, 2026
Total with taxes and fees
Cozy Home, Wood-burning Fireplace, Ski Belleayre

Spacious Catskill Mountains ski cabin with fire pit

Spacious Catskill Mountains ski cabin with fire pit
Maplecrest
9.8 out of 10, Exceptional, (19)
"The house was exactly what we were looking for! Close to the ski mountains, town and made for a really nice weekend away!"
United States
Lauren P.
$374 nightly
The price is $404
Jan 4 - Jan 5, 2026
Total with taxes and fees
Spacious Catskill Mountains ski cabin with fire pit

Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge

Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge
Hunter Highlands
9.8 out of 10, Exceptional, (9)
"Took a quick trip up to Hunter Mountain and needed a place to stay. We found a winner, very comfortable and clean with some nice amenities! Max (the owner) was an absolute pleasure to deal with.....highly recommended. "
United States
John M.
$198 nightly
The price is $215
Jan 20 - Jan 21, 2026
Total with taxes and fees
Only Ski In Out on Hunter Mtn, Panoramic Views! Hike, Golf, Fish, Recharge

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (29)
"Very clean, beautiful property! Would highly recommend staying here, and we will be coming up again someday. The host provided everything and was very diligent on the details that make this a wonderful and unique place to stay"
United States
Nick A.
$342 nightly
The price is $369
Jan 3 - Jan 4, 2026
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Catskill Kaaterskill Cabin Hot Tub FirePit Sauna
Lanesville
9.8 out of 10, Exceptional, (17)
"Simply perfect! This house was clean, fully stocked of all necessities and optimally located for hiking, town hoping, art seeing and brewery bouncing. Would love to come back in the winter for its proximity to Hunter Mountain. Highly recommend!"
United States
Sarah P.
$449 nightly
The price is $452
Jan 11 - Jan 12, 2026
Total with taxes and fees
Catskill Kaaterskill Cabin Hot Tub FirePit Sauna

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
4.0 star property
Durham
10.0 out of 10, Exceptional, (2)
"Was close to where we were attending a wedding and big enough to house us all!"
United States
Paul m.
$509 nightly
The price is $549
Jan 5 - Jan 6, 2026
Total with taxes and fees
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit

Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly

Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly
Roxbury
10.0 out of 10, Exceptional, (10)
"This cabin was the cutest. Lots of charm and character with a beautiful view! "
United States
Stephanie G.
$219 nightly
The price is $241
Jan 11 - Jan 12, 2026
Total with taxes and fees
Mountainscape: Peaceful and Skiing Getaway. Pet-Friendly

Jessie's Harvest House

Jessie's Harvest House
Tannersville
$192 nightly
The price is $203
Jan 5 - Jan 6, 2026
Total with taxes and fees
Jessie's Harvest House

Relaxing Mountain Hideaway - Hot Tub & Outdoors

Relaxing Mountain Hideaway - Hot Tub & Outdoors
2.0 star property
Hensonville
$619 nightly
The price is $669
Jan 5 - Jan 6, 2026
Total with taxes and fees
Relaxing Mountain Hideaway - Hot Tub & Outdoors

Cold Spring Lodge - Cabin 2

Cold Spring Lodge - Cabin 2
Big Indian
9.6 out of 10, Exceptional, (4)
"We had a nice relaxing stay"
United States
Michael
$248 nightly
The price is $278
Jan 22 - Jan 23, 2026
Total with taxes and fees
Cold Spring Lodge - Cabin 2

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.6 out of 10, Exceptional, (14)
"Beautiful location in a well kept property! Highly recommend it."
United States
Robert
$252 nightly
The price is $272
Jan 5 - Jan 6, 2026
Total with taxes and fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
Shandaken
10.0 out of 10, Exceptional, (1)
"10/10 experience. beautiful cabin, super cozy"
United States
Hunter W.
$178 nightly
The price is $199
Jan 26 - Jan 27, 2026
Total with taxes and fees
Modern Cottage 2 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham

2-bedroom in Peaceful Middleburgh Vroman’s Nose View

2-bedroom in Peaceful Middleburgh Vroman’s Nose View
2.5 star property
Middleburgh
10.0 out of 10, Exceptional, (1)
"Janelle was very welcoming and accommodating. The house was decorated for the holidays and very clean, comfy, and cozy. There are wonderful amenities such as pool, fire pit, grilling area, if the weather allows for outdoor activities. "
United States
Lisa C.
$254 nightly
The price is $285
Jan 4 - Jan 5, 2026
Total with taxes and fees
2-bedroom in Peaceful Middleburgh Vroman’s Nose View
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

Find out more about Ashland

Everything you need to know about Ashland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Ashland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Ashland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Ashland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Ashland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Ashland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $125 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Ashland rentals

At Expedia, we put the best Ashland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Ashland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Ashland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Ashland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Ashland?

Yes, we offer vacation rentals near popular attractions in Ashland, or you can choose a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Ashland has to offer?

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!: This vacation home rental near Ashland is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Ashland?

With 6 Expedia vacation rentals, you're sure to find just the right place for your Ashland stay.

What can I see and do in Ashland?

While exploring the area, visit family-friendly sights like Hobart Book Village, or get outside and enjoy nature at Mountain Top Arboretum. Ashland Town Hall and Hunter Mountain are a couple of places you'll find in the larger area.

What are vacation rentals like in Ashland?

Vacation rentals are private properties you can book for several days or longer in Ashland. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip.