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Compare 113 Cottages in Highland with updated reviews, rates, and availability.

Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (194)
"My sister and I needed a quick getaway from the world and found refuge in this sweet little cottage that is right on the creek. The cottage was pristine, fully eqipped, quiet and tastefully decorated. My communication with the owner, Jane, was "easy breezy". Our favorite part of our stay were the sights and sounds of the water! It was truly magnificent. We came to the cottage a little tired from the pressures of life but left rejuvenated and filled with peace. Our short stay was delightful. We...
The price is $159
$324 total
includes taxes & fees
May 15 - May 16
Streamside Cottage Walking Distance to Town of Woodstock
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
10.0 out of 10, Exceptional, (37)
"A perfect location and the cottage was set up with great attention to detail. Everything was very clean and comfortable. The property is beautiful too. John and Mollie are very responsive hosts and provided us with anything we needed. Could not ask for more. Highly recommend!"
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
10.0 out of 10, Exceptional, (71)
"We loved the cottage and it’s great location a very peaceful setting and the owner gave attention to small details that made for a very nice stay."
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
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Romantic + historic artist cottage with storybook charm in private woods!
10.0 out of 10, Exceptional, (58)
"The house was very quiet and comfortable . We enjoyed it very much and will definitely come back."
Romantic + historic artist cottage with storybook charm in private woods!
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
10.0 out of 10, Exceptional, (2)
"The property was perfect for a stay in the Hudson Valley, and perfect for anyone wanting to be near Beacon, NY specifically. The property itself (a small but modern cabin like property) was really lovely. Modern kitchen and bathroom (spacious bathroom with a spa like shower) and even had laundry. Nice outdoor space as well to have a few friends over. The owners were super responsive to questions/support during the stay. Easy on street parking at the location. Would recommend it to anyone!"
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
Dreamy Hudson Valley Cottage w/ State Park Views
10.0 out of 10, Exceptional, (2)
"This is a great cozy retreat. Clean. Everything you need, including firewood for the wood stove.Convenient to NY State Parks and not far from the Empire Trail and Hudson Valley Greenway so perfect for us to check off some of our NY State Parks Centennial Challenge tasks and get some hiking and biking in. It was perfect for the 2 of us. Ashley responded promptly to all of our communications and was a great host. Nice little touches like a basket of snacks added to the charm of this cozy cottage."
Dreamy Hudson Valley Cottage w/ State Park Views
RETREAT TO SPENCER COTTAGE Relax w. Friends Family
10.0 out of 10, Exceptional, (3)
"We rented the cottage for a girls weekend. My daughters and i enjoyed the cottage and all it had to offer. The cottage was perfect and the view from the deck was breathtaking. I hope we get the opportunity to sray here again."
RETREAT TO SPENCER COTTAGE Relax w. Friends Family
Relaxing Catskill Mountain Cottage.
10.0 out of 10, Exceptional, (37)
"This was something like our fourth stay in the cabin, and we continue to absolutely love it. Clean, comfy, cozy, aesthetically pleasing (Catskills + art), great kitchen equipment, really thoughtful and available property manager and hosts. Our little dog comes with me and my five-year-old daughter, and we're grateful she can -- and that the place doesn't scream "dog-friendly." If you don't have dogs, you won't realize that anyone else ever did. Beds and bedding clean, fragrance-free (per our...
Relaxing Catskill Mountain Cottage.
Country Cottage Retreat
10.0 out of 10, Exceptional, (9)
"we had a wonderful time! the cottage was very comfortable and really well-appointed. We made the most of the fireplace and our two dogs loved the access to the field and woods nearby. Susanne, the host, gave us great directions and was super friendly and helpful and we really appreciated the scones,chocolate and fresh local eggs left for us. We made the most of the easy access to the Rhinebeck restaurtants and hikes in the area and would love to come back! Thank you"
Country Cottage Retreat
Reset and Relax in Luxury Cottage
10.0 out of 10, Exceptional, (23)
"This is a nice place near the Omega Institute, tucked away with a nice woodsy walk in the neighborhood. The host cares about the quality of your stay. Nice, simple, clean, comfortable, everything you need. I will look to stay again in the future."
Reset and Relax in Luxury Cottage
Charming Cottage with Expansive Hudson River Views
10.0 out of 10, Exceptional, (7)
"Our stay couldn't have been better! We're two friends who were celebrating our birthdays and were here for a relaxing week of vacation. The cottage itself, the amenities, host, and location were all great. It's tucked away in a quiet neighborhood with lovely views of the river, five minutes away from Kingston (where we saw a concert at the Ulster Performing Arts Center, had a top-notch dinner at The Brickmen, and shopped at the vinyl stores). Maria was a perfect host and we loved seeing her son...
Charming Cottage with Expansive Hudson River Views
Be in Nature at this Gorgeous Riverfront Cabin
10.0 out of 10, Exceptional, (6)
"A great place to stay. Clean, stylish, and well appointed with great views and access to a small river. Highly recommend!!"
Be in Nature at this Gorgeous Riverfront Cabin
Private Guest Cottage @ The Sheeley House in High Falls NY.
10.0 out of 10, Exceptional, (1)
"Very beautiful surroundings. Manager Rob very helpful."
Private Guest Cottage @ The Sheeley House in High Falls NY.
Mountain View escape
10.0 out of 10, Exceptional, (24)
"We had an excellent stay at this cabin. Check-in and checkout were smooth and easy. The interior was super cozy, well-decorated, and very clean, with an impressively well-stocked kitchen. Almost all the major hikes in the area were 10-15 minutes away, and New Paltz was just as close. Aster was very responsive and gracious as a host, and even allowed us to stay a few extra hours so we could watch the solar eclipse from the backyard. Only regret was not making use of the fire pit."
Mountain View escape
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
10.0 out of 10, Exceptional, (12)
"Celebrated our wedding anniversary with a weekend away here. Very convenient to pretty much everything in the area. Cottage was immaculate, comfortable, and quiet! Wind chimes outside captured a windy night like a little symphony (if you're a light sleeper I'd recommend ear plugs just in case!). I'd come back to Lily Cottage in a heartbeat if I was spending another weekend up here."
Lily Cottage - a cozy accomodation moments from the beautiful Ashokan reservoir
Whimsical Woodland Cottage in Stone Ridge NY
10.0 out of 10, Exceptional, (6)
"My husband and adult son stayed here for a Hudson Valley holiday. This place is truly perfect for 2 people for a lovely getaway. Would have loved to be here in warmer weather to enjoy the front porch and firepit. It is decorated adorably. Best highlights: owner quick to respond, very comfy beds and cozy, warm gas fireplace. Just know that it is rustic cabin-like, so if you’re seeking more upscale then recommend other places. No shades except in the bedroom, no closet/dresser/place to hang or...
Whimsical Woodland Cottage in Stone Ridge NY
Classic Cottage with Beauitiful Catskill View
10.0 out of 10, Exceptional, (44)
"This was our family's (of 3) second stay at the Highland cottage, and it won't be our last! I love the charm of the place and the quiet and peaceful surroundings. Communications with the property owners are superb, and they keep the accommodations in top form. We look forward to returning!"
Classic Cottage with Beauitiful Catskill View
Leggett Cottage, High Falls, NY.
10.0 out of 10, Exceptional, (62)
"The house is a well appointed one bedroom with a nicely done kitchen and kitchen equipment. The layout is comfortable and the host's art and the other art in the home makes it a fun place to stay. We enjoyed the stay and would gladly return!"
Leggett Cottage, High Falls, NY.
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
10.0 out of 10, Exceptional, (110)
"Beautiful, immaculate cottage within walking distance to everything Woodstock. Pet friendly with every amenity you’d need for a comfortable stay. Will most definitely return."
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
10.0 out of 10, Exceptional, (156)
"My partner and I absolutely loved Brook Cottage. The pictures in the listing are very accurate. From the moment we walked in we felt at home. The cottage is warm, cozy, and very clean. The location couldn’t be better- we’d walk to the market and bakery everyday. We enjoyed cooking more than going out. Judy and Chelsea were attentive and easy to communicate with. We were able to really unplug and slow down, we had an absolutely wonderful stay."
TOP RATED Romantic rustic luxury + flowing stream + walk to town = Brook Cottage
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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.

Other property types in Highland

Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.6 out of 10, Exceptional, (18)
"Wow Ryan, the owner was really nice guy just a great place to relax and enjoy firepit,.mountain views, outdoor sitting with tv, very private!!! I'll give this one 10+ review!!!!!"
The price is $215
$280 total
includes taxes & fees
May 2 - May 3
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
The Farm at Hyde Park
9.6 out of 10, Exceptional, (45)
"We booked the Chapel for a quick weekend to check out the FDR Home and other sights around Hyde Park and Dutchess County. The place was perfect for our needs! Glen was very helpful and communication was excellent. We loved that the property has chickens and a wild turkey."
The Farm at Hyde Park
Hotel Woodstock - Iris suite
9.6 out of 10, Exceptional, (45)
"Cool propertry in a unique town"
The price is $99
$220 total
includes taxes & fees
May 2 - May 3
Hotel Woodstock - Iris suite
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.

Highland Cottages information

Number of reviews
636
Accommodation
113 Cottages
Lowest Price
$159
Highest Price
$159

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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.

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