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Holiday Rentals in Town of Highland

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Our top choices for Town of Highland holiday rentals

Holiday Home in Highland Lake

Sweet Old Farmhouse in a Tranquil Setting
3.0 star property
10.0 out of 10, Exceptional, (2)
"The property was very easy to access and easy to navigate the area with the location. Also right across from the local yoga studio was a bonus!"
United States
Anne H.
The price is €278
includes taxes & fees
17 Jan - 18 Jan 2026
Sweet Old Farmhouse in a Tranquil Setting
9.6 out of 10, Exceptional, (4)
"Overall it was comfortable. Could have used a small table in kitchen to eat at. Wasn’t stocked with enough kitchen essentials.. two small pans needed replacing and owner was very responsive and thankful for the ideas. Beds and pillows were comfortable. Back deck had nice lighting and clean grill but lacked ambiance because of placement of garbage pails. Owner said they would move them next time. We would return but felt it was too pricey for a place with no A/C!"
United States
Anthony G.
Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
10.0 out of 10, Exceptional, (2)
"I can’t put into words the feel of Enchanting River front. The location is BEAUTIFUL. Being able to fall asleep to the sound of the flowing water was just heaven. John is an incredible host, and I can’t wait for my next visit! "
United States
Britney P.
The price is €672
includes taxes & fees
25 Dec - 26 Dec
Enchanting River - Waterfront A Frame Cabin
The price is €109
includes taxes & fees
23 Dec - 24 Dec
Okama Abon Bell Tent, River View Taino Woods 15 minutes to Bethel Woods Concerts
10.0 out of 10, Exceptional, (2)
"My husband, dog, and I had a wonderful stay at the domes! It is the perfect nature getaway with all the amenities you get from a hotel! The host was very personable when we arrived and had great communication before and during our stay! The property of the domes is beautiful. We highly recommend!"
United States
Nancy B.
The price is €388
includes taxes & fees
6 Jan - 7 Jan 2026
Domes at Catskills a lakefront glamping adventure for adults
3.0 star property
The price is €263
includes taxes & fees
30 Dec - 31 Dec
Hike & Fish: Outdoor Retreat Near Trails

Cabin in Greentown

The Rex Hotel
3.5 star property
9.6 out of 10, Exceptional, (29)
"Place was very cozy, clean and relaxing"
United States
Racquel
The price is €180
includes taxes & fees
15 Jan - 16 Jan 2026
The Rex Hotel
9.4 out of 10, Exceptional, (11)
"A little off the beaten path, but a lovely Vrbo with excellent amenities with a nice natural surrounding."
United States
Nicholas G.
The price is €268
includes taxes & fees
23 Dec - 24 Dec
Serene lakeside oasis - fast WiFi 1.5 hrs from NYC, fire-pit & nature all around

Cabin in Greentown

Ferncrest Campground
3.0 star property
9.4 out of 10, Exceptional, (16)
"Attentive staff, very detailed information about the campground. Gorgeous, rustic yet fantastic facilities. Second year visiting and we’ll be back!"
United States
Penrhyn
The price is €195
includes taxes & fees
12 Jan - 13 Jan 2026
Ferncrest Campground

Holiday Home in Forestburgh

Cozy Creek House in Forestburgh
2.0 star property
10.0 out of 10, Exceptional, (1)
"Awesome place! Everything you needed there, heck they even supplied laundry detergent!"
United States
Fred
Cozy Creek House in Forestburgh
10.0 out of 10, Exceptional, (9)
"The owner was very kind and helped us with directions and recommendations for eateries around the area. "
United States
Jody
The price is €268
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Cabin with Fireplace, Firepit, Close to Lake
10.0 out of 10, Exceptional, (7)
"The house was adorable! It had all amenities. The hosts were super responsive. Definitely would stay there again. "
United States
Chris L.
The price is €206
includes taxes & fees
11 Jan - 12 Jan 2026
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
10.0 out of 10, Exceptional, (4)
"Lovely quaint stay!"
United States
Kelly G.
The price is €342
includes taxes & fees
12 Jan - 13 Jan 2026
Couple's Serenity Cabin * Hot Tub *Lake

Holiday Home in Swan Lake

In the cloud ~your cozy lake house
9.6 out of 10, Exceptional, (103)
"I loved this place. So beautiful and well furnished. "
United States
Kayla S.
The price is €292
includes taxes & fees
23 Dec - 24 Dec
In the cloud ~your cozy lake house
10.0 out of 10, Exceptional, (6)
"Great little cottage close to Bethel Woods."
United States
Erin
The price is €245
includes taxes & fees
24 Dec - 25 Dec
Cozy Cottage with Woodstock Scavenger Hunt
3.0 star property
10.0 out of 10, Exceptional, (1)
"Excellent Vacaciones Places Instagram and Facebook recommended your Property "
United States
Ronny
The price is €457
includes taxes & fees
30 Dec - 31 Dec
15 Mi to Ski Big Bear: Gem w/ Deck & Game Room
10.0 out of 10, Exceptional, (22)
"Everything was perfect with this stay. It was close to Bethel woods and Callicoon. "
United States
Lorraine G.
The price is €212
includes taxes & fees
23 Dec - 24 Dec
8 minutes to Bethel Woods! Apt. 1 is on the First Floor and newly remodeled

Cabin in Rock Hill

Trails Head Cabin
9.8 out of 10, Exceptional, (98)
"Really cozy stay I definitely have to come back during the summer months it was a beautiful experience !"
United States
Kimaya
The price is €157
includes taxes & fees
23 Dec - 24 Dec
Trails Head Cabin
10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay. A nice quiet location. We had breakfast, lunch, and drinks and dinner on the little front patio. We will be coming back!! "
United States
June D.
The price is €249
includes taxes & fees
4 Jan - 5 Jan 2026
NEW! Chic Catskills Bungalow Getaway / Hiking/Rail Trail

Cabin in Cuddebackville

Serene Rustic Retreat with Lake
2.0 star property
10.0 out of 10, Exceptional, (8)
"Amazing stay and beautiful home!"
United States
Koby A.
The price is €425
includes taxes & fees
4 Jan - 5 Jan 2026
Serene Rustic Retreat with Lake
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 Town of Highland Hotel Reviews

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Holiday Homes in Town of Highland

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