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Featured Cottages in Highland

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (250)
"A beautiful quiet setting! "
Streamside Cottage Half Mile to Town of Woodstock

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (15)
"The gatehouse was a perfect spot for a girls trip getaway. Secluded enough, but close to some local activities and restaurants! Cozy vibe and place had everything we needed!"
Charming Cottage in the Heart of the Shawangunks

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (73)
"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (20)
"An ideal retreat. The modern cabin offered serene surroundings with stunning views of the woods and creek. The property was well-maintained, and the property manager was highly responsive. A perfect choice for a peaceful and refreshing getaway."
Be in Nature at this Gorgeous Riverfront Cabin

Cedar Cottage with hot tub as seen in New York Times escape section.

9.4 out of 10, Exceptional, (84)
"Diana’s property was the perfect spot to reconnect with old friends. We enjoyed the art, food and music of Woodstock and a side trip to Bethel to check out the Woodstock Museum. Diana’s home was a comfortable place to retreat to after our days of exploring. We would love to make it an annual event. "
Cedar Cottage with hot tub as seen in New York Times escape section.

TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

10.0 out of 10, Exceptional, (167)
"Great holiday weekend. Hiked, ate, shopped and enjoyed music at Levon’s. "
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage

Relaxing Catskill Mountain Cottage.

10.0 out of 10, Exceptional, (50)
"Nice place. Beautiful seroundings"
Relaxing Catskill Mountain Cottage.

Private Woodstock cottage. Don't forget your dog!

10.0 out of 10, Exceptional, (11)
"Perfect for a visit to Woodstock. Comfortable bed, small space but everything that was needed was there. On site close parking is a plus. Great stay for a couple. "
Private Woodstock cottage. Don't forget your dog!

Mountain View escape

10.0 out of 10, Exceptional, (64)
"It’s adorable exactly What’s on the photos and equipped with everything you need for your stay definitely will be visiting it again. "
Mountain View escape

Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

10.0 out of 10, Exceptional, (42)
"Great home base for our long weekend of music and hiking. Very clean. Host is responsive. "
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Whimsical Woodland Cottage in Stone Ridge NY

9.4 out of 10, Exceptional, (10)
"The whimsical cottage was very cute and comfortable. It was clean to the naked eye, however there were cobwebs in the windowsill behind the sofa. I wanted to go sit on the Adirondack chairs behind the house it those have not been wiped down at all. The shower is very small and dark. I realize it is an amenity to have its and pans however they definitely can be updated, it is hard to cook anything on an uneven pan. Overall it was a nice stay"
Whimsical Woodland Cottage in Stone Ridge NY

NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

9.8 out of 10, Exceptional, (135)
"We had a marvelous visit!"
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

Scenic Hudson Valley Getaway • Farms & Vineyards

10.0 out of 10, Exceptional, (1)
"It was exactly what my family and I needed. A cozy, quiet place to stay with mountain views. The owner is responsive and communicates quickly. Will come back again."
Scenic Hudson Valley Getaway • Farms & Vineyards

Cute Cottage w/ Hot Tub, Pond, and Rain Deck

8.8 out of 10, Excellent, (6)
"excellent experience, environment was cozy and inviting "
Cute Cottage w/ Hot Tub, Pond, and Rain Deck

Leggett Cottage, High Falls, NY.

10.0 out of 10, Exceptional, (77)
"Lovely view of horse farm from cottage patio. Close to great hiking, the farmer’s market, and restaurants. Wonderful hosts, very helpful and responsive to all needs. "
Leggett Cottage, High Falls, NY.

Charming 2-bedroom cottage with large deck in beautiful Accord NY.

10.0 out of 10, Exceptional, (14)
"It was better than the pictures! Very peaceful and a lovely little house. Judy was very responsive with any questions or needs we had. "
Charming 2-bedroom cottage with large deck in beautiful Accord NY.

18th Century Rosendale Cottage w/pool

10.0 out of 10, Exceptional, (2)
"Beautiful place. The house had everything we couldve possibly needed. Can't wait to come back again!!"
18th Century Rosendale Cottage w/pool

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (43)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro

Magnificent Lake View

2.0 star property
Magnificent Lake 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 Highland Hotel Reviews

Find out more about Highland

Find out more about Highland

Highland Cottages information

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125 Cottages
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Frequently asked questions

What is there to do in Highland near my cottage?
If you want to explore the best of Highland, pay a visit to Franny Reese State Park. It's a hit among tourists and locals alike.