Photo by Karen Wirtz

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Compare 108 Cottages in Highland with updated reviews, rates, and availability.

Mountain View escape
Exterior

Mountain View escape

10.0 out of 10, Exceptional, (46)
"We had an extremely great time at this rental house and were blown away how the layout of the house provided all our conveniences. It was clean spacious and beautifully arranged as seen in pics online . It was our mountain escape dream and we would definitely recommend and stay here again ."
Mountain View escape
Reset and Relax in Luxury Cottage
Interior

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
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
View of Herb Cottage from the 'show off' herb garden

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

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

10.0 out of 10, Exceptional, (27)
"We had a wonderful stay in this quiet gem. Clean, comfortable, cute, and cozy. Highly recommended! "
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Charming 2-bedroom cottage with large deck in beautiful Accord NY.
Living area

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.
Stony Kill Ranch - Bohemian Paradise on Minnewaska

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 1800's Cornwall-On-Hudson Cottage!
Cornwall-On-Hudson Vacation Rental | 2BR | 2BA | Stairs Required | 2,000 Sq Ft

Historic 1800's Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (22)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic 1800's Cornwall-On-Hudson Cottage!
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
The loft also overlooks the spacious living room…

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

10.0 out of 10, Exceptional, (163)
"Great location, beautiful cottage and property."
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
Be in Nature at this Gorgeous Riverfront Cabin
Wappinger Cottage on a Summer Evening

Be in Nature at this Gorgeous Riverfront Cabin

10.0 out of 10, Exceptional, (13)
"Property was as advertised. Clean and nearby places we wanted to visit while, still being out of the way and quiet."
Be in Nature at this Gorgeous Riverfront Cabin
A Cozy Farmstead Cottage Amidst Two Barns in Hudson Valley
Hand-hewn beams & cathedral ceilings

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
Retreat to Tranquil Cottage 65 Min from NYC - Onsite Parking, Pet-Friendly
Living area

Retreat to Tranquil Cottage 65 Min from NYC - Onsite Parking, Pet-Friendly

6.8 out of 10, (19)
"Contacted host on the morning of stay about instructions to access house. Had not received them. Cancelled on me shortly after."
The price is AED 771
AED 1,427 total
includes taxes & fees
4 Jan - 5 Jan
Retreat to Tranquil Cottage 65 Min from NYC - Onsite Parking, Pet-Friendly
Streamside Cottage Half Mile to Town of Woodstock
Front Entrance to Cottage

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (226)
"Place was a perfect place to unwind. Very clean and Jane was very communicative!"
Streamside Cottage Half Mile to Town of Woodstock
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Teahouse

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (40)
"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 AED 661
AED 1,006 total
includes taxes & fees
5 Jan - 6 Jan
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Relaxing Catskill Mountain Cottage.
Main room

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.
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, (58)
"Perfectly cute and cutely perfect "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

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 ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Living area

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

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 ~ In town ~ fenced in yard ~ Hot Tub ~ Pets welcome!
Whimsical Woodland Cottage in Stone Ridge NY
Curl up on this plush, gorgeous leather couch next to a picture perfect fire.

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
Dreamy Hudson Valley Cottage w/ State Park Views
Garrison Vacation Rental | 1BR | 1BA | 650 Sq Ft | Steps Required

Dreamy Hudson Valley Cottage w/ State Park Views

9.8 out of 10, Exceptional, (12)
"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
House surrounded by pine trees

Cedar Cottage with hot tub

9.4 out of 10, Exceptional, (80)
"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
Property grounds

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

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

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 AED 790
AED 1,115 total
includes taxes & fees
4 Jan - 5 Jan
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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