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Featured Cottages in Highland and around

Charming Cottage in the Heart of the Shawangunks
Exterior

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (16)
"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
Exterior

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

10.0 out of 10, Exceptional, (74)
"Nice property Very clean and comfortable "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Be in Nature at this Gorgeous Riverfront Cabin
Exterior

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (21)
"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
Pet-friendly Cottage at Historic Millbrook Farm Estate
Exterior

Pet-friendly Cottage at Historic Millbrook Farm Estate

9.2 out of 10, Wonderful, (14)
"Great location, neat and tidy. Hosts are great, too."
Pet-friendly Cottage at Historic Millbrook Farm Estate
Streamside Cottage Half Mile to Town of Woodstock
Exterior

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (253)
"A beautiful quiet setting! "
Streamside Cottage Half Mile to Town of Woodstock
Relaxing Catskill Mountain Cottage.
Exterior

Relaxing Catskill Mountain Cottage.

10.0 out of 10, Exceptional, (50)
"Nice place. Beautiful seroundings"
Relaxing Catskill Mountain Cottage.
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
Exterior

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

10.0 out of 10, Exceptional, (80)
"My friend and I really enjoyed the solace of our stay. Highly recommend!"
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
Woodstock Cottage with hot tub. Close to town yet very private.
Exterior

Woodstock Cottage with hot tub. Close to town yet very private.

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. "
Woodstock Cottage with hot tub. Close to town yet very private.
Scenic Hudson Valley Getaway • Farms & Vineyards
Exterior

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
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (43)
"Lily Cottage worked out perfectly for my wife and myself. It was clean, quiet, and amenities were as described in the listing. It was a scenic 20 minute drive to Woodstock, the Ashokan bike trail, and Phoenicia. Recommended!"
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Whimsical Woodland Cottage in Stone Ridge NY
Exterior

Whimsical Woodland Cottage in Stone Ridge NY

9.4 out of 10, Exceptional, (10)
"The cottage was in a great location and perfect for my husband and me. Nice getaway!"
The price is €262
includes taxes & fees
29 Sept - 30 Sept
Whimsical Woodland Cottage in Stone Ridge NY
Private cottage - 5 min from the center of town
Interior

Private cottage - 5 min from the center of town

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 cottage - 5 min from the center of town
Leggett Cottage, High Falls, NY.
Exterior

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.
Exterior

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.
Charming Rhinebeck Cottage, 5 min. from town, King Bed!
Property grounds

Charming Rhinebeck Cottage, 5 min. from town, King Bed!

10.0 out of 10, Exceptional, (1)
"Wonderful couples getaway. Stunning landscape, wildlife, and views."
Charming Rhinebeck Cottage, 5 min. from town, King Bed!
18th Century Rosendale Cottage w/pool
Exterior

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
Terrace/patio

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (44)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is €256
includes taxes & fees
19 Oct - 20 Oct
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Luxe Family Home on Orange Lake w/ Private Dock!
House (3 Bedrooms) | Interior

Luxe Family Home on Orange Lake w/ Private Dock!

3.0 star property
Luxe Family Home on Orange Lake w/ Private Dock!
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Exterior

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

The price is €185
includes taxes & fees
8 Oct - 9 Oct
Mondrian Manor - Cottage in the lower Catskills near Ellenville and Wurtsboro
Magnificent Lake View
Property grounds

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

The Thayer Hotel at West Point

The Thayer Hotel at West Point

10/10 Excellent
"The perfect place to stay"
LOUIS 2-night trip
Posted 3 days ago
The Thayer Hotel at West Point

Find out more about Highland

Find out more about Highland

Highland Cottages information

Number of reviews
727
Accommodation
122 Cottages
Lowest Price
€185
Highest Price
€262

Frequently asked questions

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What is there to do in Highland near my cottage?
Once you've unpacked your bags, head out and discover the wonderful things Highland has to offer. Apple Greens Golf Course is a top attraction to add to your must-see list.

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