Photo by Karen Wirtz

Search Cottages in Highland

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Compare 110 Cottages in Highland with updated reviews, rates, and availability.

Reset and Relax in Luxury Cottage

10.0 out of 10, Exceptional, (31)
"Beautiful place about a 15 minute drive out of Rhinebeck. Great views, well equipped kitchen and spacious living quarters. Bed is a king and super comfy. The hosts were so kind and accommodating with lots of great suggestions for what to do and where to eat. You’ll love it!"
Reset and Relax in Luxury Cottage

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (39)
"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 676
SAR 1,051 total
includes taxes & fees
22 Dec - 23 Dec
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Mountain View escape

10.0 out of 10, Exceptional, (43)
"Charming. Peaceful. Beautiful. Well-designed. Well-stocked. I cannot recommend this place enough. It is the ideal getaway for an individual or couple. Hope to have a reason to return soon! "
Mountain View escape

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (224)
"Place was a perfect place to unwind. Very clean and Jane was very communicative!"
The price is SAR 672
SAR 1,205 total
includes taxes & fees
27 Nov - 28 Nov
Streamside Cottage Half Mile to Town of Woodstock

Quaint village, walk to restaurants and shops.

9.8 out of 10, Exceptional, (9)
"Wonderfully quaint place within walking distance of downtown restaurants/pubs. Cant wait to come back"
Quaint village, walk to restaurants and shops.

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

10.0 out of 10, Exceptional, (58)
"Perfectly cute and cutely perfect "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

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

10.0 out of 10, Exceptional, (26)
"This property is perfect! We were staying for our anniversary and enjoyed all aspects of our stay: the proximity to all activities we wanted to do, how quiet it was, very clean and cozy. Would highly recommend. "
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir

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

10.0 out of 10, Exceptional, (6)
"We had a fabulous stay at Judy's place. The beds were very comfortable, and the location was good. When we had an issue with the furnace, the owner went out of her way to correct the problem and ensured that we were comfortable. We would recommend this place."
Charming 2-bedroom cottage with large deck in beautiful Accord NY.

Whimsical Woodland Cottage in Stone Ridge NY

9.8 out of 10, Exceptional, (7)
"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

Stony Kill Ranch - Bohemian Paradise on Minnewaska

7.4 out of 10, Good, (3)
"Some friends and our pups were looking to spend a nice weekend upstate with our dogs to relax and spend time, and this place was perfect. The location is GREAT! It is near hiking trails, some breweries/orchards and while we didn’t go to dinner, there were restaurants around as well. The house was as described, spacious and had a lot to offer. We loved spending time in the hot tub and around the fire pit. The jam shed was a lot of fun for some in our group too! Check in was easy and when we had a...
Stony Kill Ranch - Bohemian Paradise on Minnewaska

Historic Cornwall-On-Hudson Cottage w/ Deck!

10.0 out of 10, Exceptional, (21)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic Cornwall-On-Hudson Cottage w/ Deck!

Esopus Creek Cottage

Esopus Creek Cottage

Dream Cottage in the Gunks

9.6 out of 10, Exceptional, (7)
"Perfectly situated near recreational spots. Cottage is exactly as advertised. Check in SO EASY! Thank you for the coffee and tea. "
The price is SAR 205
SAR 563 total
includes taxes & fees
9 Dec - 10 Dec
Dream Cottage in the Gunks

Relaxing Catskill Mountain Cottage.

10.0 out of 10, Exceptional, (45)
"The property was absolutely beautiful well-maintained lovely! Sitting out on the deck, making dinner having cocktail listening to music talking to my spouse just what we needed! Cannot wait for reschedule"
Relaxing Catskill Mountain Cottage.

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

9.8 out of 10, Exceptional, (130)
"Lovely in every way except loft area around bed. Didn’t realize I couldn’t stand upright. Was difficult to get around. Carpet could be replaced on loft. No idea it had such challenging steps to the bed. Cottage had a musty smell when first entered. "
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

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

10.0 out of 10, Exceptional, (77)
"Nice little cozy cabin. Perfect home base for a weekend in Woodstock. Not far from town but quiet enough that I watched a pair of deer settle down and take a nap a stones throw from the back window. Perfect mix of modern amenities and rustic locale."
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

Private Home ~ All Yours ~ Newly Renovated ~ In town ~ fenced in yard ~ Hot Tub

9.8 out of 10, Exceptional, (108)
"This house couldn’t be closer to town - literally steps from our favorite restaurant. Perfect for our family of three (plus our dog) but would also work well for two couples (with a loft area that could sleep a kid or two on the couch or an air mattress). Great communication with our host who was super responsive and accommodating. All the amenities we needed and the hot tub was a great bonus. We’d stay again in a heartbeat! "
Private Home ~ All Yours ~ Newly Renovated ~ In town ~ fenced in yard ~ Hot Tub

Romantic + historic artist cottage with storybook charm in private woods!

10.0 out of 10, Exceptional, (59)
"Jill made everything really easy with clear instructions for the house and finding the place . Really nice few days in a beautiful and historic house in a beautiful part of the country "
Romantic + historic artist cottage with storybook charm in private woods!

Dreamy Hudson Valley Cottage w/ State Park Views

9.8 out of 10, Exceptional, (11)
"Absolutely gorgeous house! Great location and a beautiful view from the porch. Would highly recommend to anyone. "
Dreamy Hudson Valley Cottage w/ State Park Views

Cedar Cottage with hot tub

9.4 out of 10, Exceptional, (79)
"Comfortable, spacious, beautiful grounds, lovely porch/sun room"
Cedar Cottage with hot tub
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 Scenic Mansion With Breathtaking View

9.6 out of 10, Exceptional, (11)
"So nice we keep coming back. Can't recommend highly enough and will be back in the spring. "
The Scenic Mansion With Breathtaking View

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

10.0 out of 10, Exceptional, (1)
"Really liked that each room had it's own temperature control"
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!

9.8 out of 10, Exceptional, (26)
"This place was great! The apartment itself is a great size for 2 people. The yard was pretty big with lots of seating, firepit, an awesome guitar shaped chiminea, nice sized pool, outdoor tv in the gazebo. The owner, Ryan, came later at night and left the next morning. He was super nice and very helpful!"
The price is SAR 807
SAR 1,159 total
includes taxes & fees
30 Nov - 1 Dec
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
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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