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Highland Vacation Rentals

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Vacation Rentals in Highland

Property grounds
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 CA $294
CA $387 total
includes taxes & fees
May 16 - May 17
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
Fridge, microwave, oven, stovetop
The Scenic Mansion With Breathtaking View
9.4 out of 10, Exceptional, (3)
"We loved staying in this large home for a weekend wedding in the area. All couples had plenty of room, with a bathroom in every bedroom, comfy beds, lots of living spaces, and gorgeous views of the valley below. The fall colors were so pretty!"
The Scenic Mansion With Breathtaking View
Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (196)
"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 CA $217
CA $437 total
includes taxes & fees
May 16 - May 17
Streamside Cottage Walking Distance to Town of Woodstock
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Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (47)
"Very unusual, appealing proportions, well stocked, perfect location"
The Farm at Hyde Park
Property grounds
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very good, (37)
"Our trip was amazing. We do it again again and again"
The price is CA $171
CA $198 total
includes taxes & fees
May 19 - May 20
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, (30)
"This place is wonderful!!!! It was a beautiful stay."
The price is CA $258
CA $512 total
includes taxes & fees
May 16 - May 17
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
View from property
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
10.0 out of 10, Exceptional, (152)
"this was one of the most comfortable, easy to navigate vacation homes we have ever had. we used the grill, kitchen had everything you need, the deep sinks made washing dishes easy, (there was a dishwasher. but we didn't use it), windows allowed a 180 degree view of the back yard and forest beyond, where we saw a family of deer. Everyone slept like babies on mattresses that were heavenly! Or was super available and responsive to questions. A hannaford super market is 2.3 miles away. Bread Alone...
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, (35)
"Very nice property, immaculately clean and very close to the Riverside Art Venue. Both quiet and convenient for my time in Newburgh. I would definitely stay here again."
The price is CA $109
CA $243 total
includes taxes & fees
May 27 - May 28
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Property grounds
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, (81)
"We enjoyed our stay at this property. The location is very private and comfortable. The kitchen is well stocked with amenities."
The price is CA $113
CA $368 total
includes taxes & fees
May 21 - May 22
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Property grounds
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (32)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is CA $246
CA $381 total
includes taxes & fees
Jun 2 - Jun 3
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (64)
"This is our 4th time staying here! And it won't be the last. Weather perfect for sitting on the deck with coffee and cocktails watching the creek slowly flow by. Beds are super comfortable with the BEST pillows. Everything you need for a relaxing stay. O.J, incredible bread with butter and strawberry preserves to greet you! Only a mile from town. An easy walk. Will see you again soon!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Property grounds
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (13)
"Our stay was quite nice, the place looked as the pictures showed it to be which is just amazing. everything was music themed and our host had an amazing selection of vinyls. The only complaints I would say I had was the small flying bugs near the Tv and we weren’t provided paper towels. Overall it was a nice place for the night and the property itself was beautiful."
The price is CA $197
CA $290 total
includes taxes & fees
May 27 - May 28
Mid-Century DJ’s Dream
Exterior
Cabin in the heart of the Hudson Valley, Cabin 4
8.4 out of 10, Very good, (11)
"Everything was as it says it was. Place was spotless. In the evening and morning you didn’t hear any traffic noise at all. Was quiet and peaceful. Communication with the property owner was outstanding."
The price is CA $149
CA $223 total
includes taxes & fees
May 19 - May 20
Cabin in the heart of the Hudson Valley, Cabin 4
Exterior
The Studio at the Inn at High Falls
8.4 out of 10, Very good, (17)
"Love staying at The Studio at the Inn at High Falls. It truly is my new home away from home. Soo Clean, Comfortable and incredible friendly helpful people who own and work there. Again Thank you Frank and too a New Year. Patricia"
The price is CA $171
CA $353 total
includes taxes & fees
May 16 - May 17
The Studio at the Inn at High Falls
Exterior
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
Property grounds
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
10.0 out of 10, Exceptional, (11)
"Perfect spot to visit grandkids Lots to do"
The price is CA $157
CA $335 total
includes taxes & fees
May 21 - May 22
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (16)
"Matt is a wonderful host! I was very impressed by the cleanliness of the 1 bedroom cabin and how much thought went into providing guests with everything they need. I stayed for four nights and was very comfortable. The bed was so comfortable I slept great. Kingston is a city so some noise is expected. The neighborhood is very quiet at night and you can hear a little noise occasionally in the distance. Matt provides an adjustable sound machine. I put it on low and slept like a baby. Matt is very...
The price is CA $116
CA $286 total
includes taxes & fees
May 21 - May 22
Campfire Cottage: Fireplace, fire pit & no chores!
Property grounds
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (30)
"It was a nice location to spend time with family."
Cozy Relaxing Retreat in Saugerties, NY
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (39)
"Quiet, clean and very comfortable. Beautiful property located just minutes from town. Will definitely stay here again."
The price is CA $205
CA $294 total
includes taxes & fees
Jun 4 - Jun 5
Cozy country efficiency in the Hudson Valley
Don't see what you're looking for?
See all available properties in Highland
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 Vacation Rental Travel Info

Number of vacation rentals
2
Popular accommodation
Highland private vacation homes
Known landmarks
Benmarl Vineyards and Winery, Glorie Farm Winery and Benmaryle Wineries
International airport
Newburgh, NY (SWF-Stewart Intl.)

Other types of properties in Highland you may be interested in

Lobby
Rodeway Inn & Suites New Paltz - Hudson Valley
2.0 star property
7.0 out of 10, Good, (548)
"This is a great motel for a cheap stay in New Paltz! If you're not looking for anything beyond a comfy bed, clean room with basic necessities like a full bathroom, microwave, tv and mini fridge. Rooms are spacious though complete with sofa and desk. Staff is friendly. Good spot to just catch some good sleep"
The price is CA $92
CA $103 total
includes taxes & fees
May 20 - May 21
Rodeway Inn & Suites New Paltz - Hudson Valley
Front of property
SureStay Plus Hotel by Best Western Highland Poughkeepsie
2.5 star property
7.6 out of 10, Good, (705)
"This hotel is a hidden gem and pet friendly. The staff was great and had coffee or tea available at all times and comfortable seating area to eat or just relax. No microwaves in rooms but available in lobby. Will go back soon. Convenient to highways. "
The price is CA $141
CA $158 total
includes taxes & fees
May 22 - May 23
SureStay Plus Hotel by Best Western Highland Poughkeepsie
Lobby
Best Western Plus Kingston Hotel And Conference Center
2.5 star property
8.0 out of 10, Very good, (1001)
"All of the staff was super friendly and helpful. The building is a little tricky to navigate. Great food in the dining area, and overall all great stay. "
The price is CA $191
CA $214 total
includes taxes & fees
Jun 2 - Jun 3
Best Western Plus Kingston Hotel And Conference Center
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.

Everything you need to know about Highland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Highland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland vacation rentals we have selected for you start as low as CA $109 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Highland rentals

At Expedia, we put the best Highland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Highland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find vacation rentals in Highland?

Yes, we offer vacation rentals close to the most popular points of interest in Highland, or you can select a more remote option if you want a relaxing place to stay. Highland is known for its riverfront and mountain views.

What are some of the best vacation home rentals in Highland?

The Farm at Hyde Park: Visitors like this Highland vacation home rental. It is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals will I find in Highland?

With 18 Expedia vacation rentals, you're sure to find just the right place for your Highland stay.

What can I see and do in Highland?

Walkway Over the Hudson State Historic Park and Berean Park Beach are a couple of scenic spots to enjoy the outdoors, whereas Franklin D Roosevelt Library & Museum is one of the cultural attractions. While here, Franny Reese State Park and Apple Greens Golf Course are other places worth a visit.

What are vacation rentals like in Highland?

Vacation rentals are privately owned properties you can book for a couple days or more in Highland. Vacation rentals offer extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.

Recent reviews of Highland properties
Expedia verified reviews

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

5/5 Excellent
"Excellent all around! Highly recommend!"
A verified traveller stayed at Inn at Bellefield / Hyde Park, Residence Inn by Marriott
Posted 16 hours ago
Inn at Bellefield / Hyde Park, Residence Inn by Marriott