Holiday Homes in Ashland

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Ashland holiday homes

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Phoenicia
9.2 out of 10, Wonderful, (35 reviews)
"Great location and charming home! The sauna was amazing. "
United States
Jessica B.
The price is €294
includes taxes & fees
16 Mar - 17 Mar
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

2-bedroom in Peaceful Middleburgh Vroman’s Nose View

2-bedroom in Peaceful Middleburgh Vroman’s Nose View
Middleburgh
10.0 out of 10, Exceptional, (1 review)
"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.
The price is €283
includes taxes & fees
13 Mar - 14 Mar
2-bedroom in Peaceful Middleburgh Vroman’s Nose View

Bear House Catskills: Private Pool, Pond & Hot Tub, WFH, Dog-Friendly

Bear House Catskills: Private Pool, Pond & Hot Tub, WFH, Dog-Friendly
Cairo
10.0 out of 10, Exceptional, (9 reviews)
"Such a lovely home with nice details and comforts - thank you for a great stay!"
United States
Liz Z.
The price is €477
includes taxes & fees
17 Mar - 18 Mar
Bear House Catskills: Private Pool, Pond & Hot Tub, WFH, Dog-Friendly

Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Hensonville
10.0 out of 10, Exceptional, (10 reviews)
"This is a very cute, very clean condo near Windham. Perfect for our family of 4. Would definitely stay again. "
United States
Kimberly K.
The price is €270
includes taxes & fees
17 Mar - 18 Mar
Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Midnight Fox

Midnight Fox
Hunter
10.0 out of 10, Exceptional, (12 reviews)
"We had a great time "
United States
israel R.
The price is €367
includes taxes & fees
15 Mar - 16 Mar
Midnight Fox

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (58 reviews)
"Everything was perfect! Great location!"
United States
Susan I.
The price is €195
includes taxes & fees
15 Mar - 16 Mar
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

The Bend: Trout Lily Suite • Pool • Sauna • Fire Pits

The Bend: Trout Lily Suite • Pool • Sauna • Fire Pits
Phoenicia
The price is €378
includes taxes & fees
18 Mar - 19 Mar
The Bend: Trout Lily Suite • Pool • Sauna • Fire Pits

Spacious 5 BR w/Mountaintop Views-2 Min to Hunter

Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
Tannersville
10.0 out of 10, Exceptional, (3 reviews)
"Great time had by all of us! House is perfect for several families and so much to do in the area. Would definitely stay again! Owners were very easy to access for questions."
United States
Michelle D.
The price is €576
includes taxes & fees
17 Mar - 18 Mar
Spacious 5 BR w/Mountaintop Views-2 Min to Hunter

West Kill Barnhouse: Ski, Work & Unwind

West Kill Barnhouse: Ski, Work & Unwind
West Kill
10.0 out of 10, Exceptional, (18 reviews)
"Great stay"
United States
Vijay S.
The price is €309
includes taxes & fees
23 Mar - 24 Mar
West Kill Barnhouse: Ski, Work & Unwind

The Bend: Stony Clove Suite • Pool • Sauna • Creek

The Bend: Stony Clove Suite • Pool • Sauna • Creek
Phoenicia
The price is €350
includes taxes & fees
23 Mar - 24 Mar
The Bend: Stony Clove Suite • Pool • Sauna • Creek

Cozy Country Farmhouse Along the Catskill Scenic Trail

Cozy Country Farmhouse Along the Catskill Scenic Trail
Hobart
10.0 out of 10, Exceptional, (127 reviews)
"We stay here year after year! It is always clean, quiet, and well stocked. It feels like home away from home. "
United States
Andrea P.
The price is €290
includes taxes & fees
18 Mar - 19 Mar
Cozy Country Farmhouse Along the Catskill Scenic Trail

Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room

Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
Hunter
9.6 out of 10, Exceptional, (13 reviews)
"⭐️⭐️⭐️⭐️⭐️ The most important part of any stay is having a great host — and we truly did! Our host was incredibly welcoming, responsive, and thoughtful, which made the entire experience so much smoother and more enjoyable. The property itself was cozy, well-maintained, and perfectly located to explore Hunter, NY. We felt right at home from the moment we arrived and left with wonderful memories. Highly recommend this place to anyone visiting the area!"
United States
Taha
The price is €546
includes taxes & fees
15 Mar - 16 Mar
Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room

Purple Victorian Vacation Home near Belleayre

Purple Victorian Vacation Home near Belleayre
Pine Hill
9.0 out of 10, Wonderful, (2 reviews)
"The host was wonderful and accommodating. The house was comfortable and we enjoyed the architecture. The location is basically at the base of the mountain. Great stay. "
United States
Paul G.
The price is €579
includes taxes & fees
16 Mar - 17 Mar
Purple Victorian Vacation Home near Belleayre

Cozy Home, Wood-burning Fireplace, Ski Belleayre

Cozy Home, Wood-burning Fireplace, Ski Belleayre
Margaretville
9.8 out of 10, Exceptional, (16 reviews)
"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.
The price is €289
includes taxes & fees
23 Mar - 24 Mar
Cozy Home, Wood-burning Fireplace, Ski Belleayre

Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking

Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking
Catskill
The price is €289
includes taxes & fees
13 Mar - 14 Mar
Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking

Fantastic 3-bedroom house right near Belleayre mountain ski center in Highmount

Fantastic 3-bedroom house right near Belleayre mountain ski center in Highmount
Pine Hill
10.0 out of 10, Exceptional, (1 review)
"The host were great communicating with us and answered all our questions. The house was super cute, well equipped with anything we needed (towels, kitchen appliances, dishes, coffee maker, etc)We would definitely stay again if we are in the area "
United States
Patricia F.
The price is €451
includes taxes & fees
13 Mar - 14 Mar
Fantastic 3-bedroom house right near Belleayre mountain ski center in Highmount

COZY COTTAGE WITH MOUNTAIN VIEW AT LAKEFRONT LOT

COZY COTTAGE WITH MOUNTAIN VIEW AT LAKEFRONT LOT
Stamford
9.4 out of 10, Exceptional, (11 reviews)
"Very spacious and in a lovely area. It was perfect for our family. "
United States
Rebecca K.
The price is €553
includes taxes & fees
13 Mar - 14 Mar
COZY COTTAGE WITH MOUNTAIN VIEW AT LAKEFRONT LOT

Modern getaway in Catskills

Modern getaway in Catskills
Cairo
10.0 out of 10, Exceptional, (13 reviews)
"The host was accommodating and the house was very nice!"
United States
Ken B.
Modern getaway in Catskills

Modern Family Retreat in the Catskills Wilderness

Modern Family Retreat in the Catskills Wilderness
Round Top
The price is €405
includes taxes & fees
17 Mar - 18 Mar
Modern Family Retreat in the Catskills Wilderness

Luxury Tiny Home Ski Cabin with Barrel Sauna Room!

Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
Arkville
10.0 out of 10, Exceptional, (24 reviews)
"A cozy and comfortable place , We had a pleasant time, Definitely worth another visit."
United States
Anonymous traveller
The price is €391
includes taxes & fees
30 Mar - 31 Mar
Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Ashland Hotel Reviews

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
353
Accommodation
543 Holiday Homes
Lowest Price
€195
Highest Price
€579