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Compare 124 Cottages in Highland with updated reviews, rates, and availability.

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (233)
"Incredible location and comfortable space. Would make this my exclusive place to stay everytime I visit woodstock."
Streamside Cottage Half Mile to Town of Woodstock

Mountain View escape

10.0 out of 10, Exceptional, (52)
"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

Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!

9.8 out of 10, Exceptional, (111)
"Just steps from everything, yet the property feels tucked away and private. We loved being able to walk everywhere and then have the cozy house to come back to - the wood burning stove made it extra cozy during our late March trip to Woodstock. Very communicative and friendly host."
Private Home ~ All Yours ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!

TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too

10.0 out of 10, Exceptional, (117)
"Myself and my partner really enjoyed our 4-night stay in the smaller half of Brook Cottage. Everything was spotlessly clean when we arrived, it is plenty spacious for two, nicely presented and very well furnished and equipped. There was nothing lacking. The cottage is set back from the road so was nice and quiet. We didn’t use the patio because of the chilly early April weather, but that too was a nice space. Located at the top end of town, it was only a short walk to shops and restaurants....
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too

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

10.0 out of 10, Exceptional, (79)
"This was just what we were looking for. The host was very quick to respond to any of my questions. We enjoyed the location and all the amenities. The outdoor grill, outdoor firepit and inside fireplace were enjoyed and it was a nice bonus that there was plenty of firewood."
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

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

10.0 out of 10, Exceptional, (61)
"Very Comfortable"
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Relaxing Catskill Mountain Cottage.

10.0 out of 10, Exceptional, (48)
"Property owner was very responsive and easily accessible. Our power was out when we got there and we were provided updates as to when everything would be restored in a timely manner. House was clean and comfortable. Would highly recommend this place to anyone looking to stay around West Shokan."
Relaxing Catskill Mountain Cottage.

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (32)
"Amazing floors, bathroom showers (wow!), and an awesome kitchen."
Reset and Relax in Luxury Cottage

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (9)
" "
The price is SAR 1,594
SAR 3,000 total
includes taxes & fees
1 May - 2 May
Charming Cottage in the Heart of the Shawangunks

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.0 out of 10, Wonderful, (42)
"2 nights in a delightful cottage. It is small but delightfully appointed. The highlight was this clean, warm little cottage is perched directly on swft stream. We left the backdoor open at night!"
The price is SAR 675
SAR 1,139 total
includes taxes & fees
4 May - 5 May
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

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

10.0 out of 10, Exceptional, (31)
"Lily Cottage is a sweet little gem!! This was first getaway as a family of three (4mo old daughter) and our beloved pup (20lb mini schnauzer!) Lily Cottage was the perfect cozy cottage to getaway for a long weekend. It had everything we needed (kitchen supplies, etc. to make a meal and a washer and dryer! (essential for a baby). The bedroom is able to accommodate a small pack and play or you could arrange it in the living space as well. Our dog also loved the small yard to get some zoomies out....
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

Chestnut on Willow Lake

The price is SAR 1,125
SAR 1,706 total
includes taxes & fees
28 Apr - 29 Apr
Chestnut on Willow Lake

Pet-friendly Cottage at Historic Millbrook Farm Estate

10.0 out of 10, Exceptional, (1)
"Stayed in this renovated farmhouse for a very snowy weekend. Nicely redone and furnished with spacious living/dining area. Could have fit 2 more adults or 2-3 kids. Hosts were lovely and introduced us to the goats. Too snowy and icy to get outdoors or explore much but local village has shops and kitchen was stocked with pantry staples and bottled water, milk/creamers for coffee so arrival day grocery run was not needed. Bonus large picture window let us enjoy the abundant snow from the warmth of...
Pet-friendly Cottage at Historic Millbrook Farm Estate

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

9.8 out of 10, Exceptional, (133)
"The cottage was a great place to stay with great easy access to downtown Woodstock, Kingston, and Rhineback. Lots of attention to detail by the owner. For example, there are plenty of kitchen utensils and dishes and tons of books and DVD's. The DVD's are displayed in alphabetical order and there are multiple heat zones that enabled the bathroom to independently be very warm while keeping the remaining zones more temperate. The place has everything you need for a cozy stay. The only...
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (16)
"Beautiful house. Really enjoyed the views even. Can only imagine what it round be like in the summer. The host always answered if I had questions and was informative with process. It was a great stay. Thank you!!!"
Be in Nature at this Gorgeous Riverfront Cabin

Historic 1800s Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (22)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic 1800s Cornwall-On-Hudson Cottage!

Leggett Cottage, High Falls, NY.

10.0 out of 10, Exceptional, (71)
"We enjoyed our time at the “artists den”. It’s clean and cozy and the location was perfect for our Minnewaska adventure. Host Anat is responsive, friendly and accommodating.We look forward to coming back in the spring and getting on the bike path that’s just down the hill.Thank you Anat and JamieHope to see you again soon"
Leggett Cottage, High Falls, NY.

A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley

9.8 out of 10, Exceptional, (52)
"Very beautiful property! Beautiful night sky views and excellent nature, perfect place for a romantic weekend"
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley

Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

9.6 out of 10, Exceptional, (7)
"Great peaceful spot, close to a ton of outdoor activities. East check in and property was as advertised."
The price is SAR 338
SAR 703 total
includes taxes & fees
28 Apr - 29 Apr
Cozy Cottage Near Hiking, Infrared Sauna & Fireplace | Dream House in the Gunks

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

9.4 out of 10, Exceptional, (83)
"The house was perfect; the hot tub was pristine, the location was remote but close enough to visit Woodstock, Kingston and Phoenicia. The communication with the owner was swift and helpful. "
Cedar Cottage with hot tub as seen in New York Times escape section.
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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Other property types in Highland

The House In Highland- Secluded Retreat

The House In Highland- Secluded Retreat

Our home is perfect for relaxing and having lots of fun, with near by activity’s

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. The host is very responsive. The location is 30 minutes from Beacon, 10 minutes from Poughkeepsie and 2 hrs from NYC. The office was a nice feature and the house has great WiFi. "
Our home is perfect for relaxing and having lots of fun, with near by activity’s

The Scenic Mansion With Breathtaking View

9.6 out of 10, Exceptional, (13)
"This house is so grand and perfect for a destination wedding, corprate retreat or family reunion. Host was wonderful!"
The Scenic Mansion With Breathtaking 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.