Photo by Karen Wirtz

Highland Vacation Rentals

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Vacation Rentals in Highland

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, 22 reviews
"The backyard was really cool! Great features. Beautiful, peaceful, and private. We did not see or hear anyone else on the property during our stay. The apartment was very nice. Cozy, clean and comfortable, perfect for two. The host, Ryan was extremely responsive and friendly. We had an amazing stay would definitely recommend!"
The price is ￥33,770
per night
Jun 17 - Jun 18
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
The Scenic Mansion With Breathtaking View
Fridge, microwave, oven, stovetop
The Scenic Mansion With Breathtaking View
9.4 out of 10, Exceptional, 3 reviews
"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
The Farm at Hyde Park
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, 49 reviews
"We needed a central location for my daughter’s bridal shower. We could not have imagined a better place. It is beautiful and so natural. Glen was helpful and welcoming. He even came over to sweep off the expansive patio before our guests arrived and this was after he made sure everyone was awake. The house was well supplied with kitchen and dining items. The grounds were perfect - lawn chairs, picnic table, fire pit and free range chickens whose eggs we were able to enjoy. We would all stay here...
The Farm at Hyde Park
Streamside Cottage Walking Distance to Town of Woodstock
Property grounds
Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, 200 reviews
"Very nice stay from start to finish. We stayed two nights after a busy conference and the space was clean and tranquil, with a gorgeous stream to relax us. "
The price is ￥29,686
per night
Jun 17 - Jun 18
Streamside Cottage Walking Distance to Town of Woodstock
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Property grounds
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, 38 reviews
"This is a nice apartment built onto a home in a nice neighborhood cul-de-sac. Beautiful views, quiet, clean. Responsive owners. The shower is small so might not be suitable for all. Enjoyed our week."
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Property grounds
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, 32 reviews
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is ￥28,332
per night
Jun 16 - Jun 17
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Exterior
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, 30 reviews
"Very charming one room apartment with bathroom and kitchen area. Beautiful surrounding you with very pleasant hosts"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Cozy Country Cottage with Basketball Court/Spa/Fireplace/Enclosed Yard/Fire Pit
Property grounds
Cozy Country Cottage with Basketball Court/Spa/Fireplace/Enclosed Yard/Fire Pit
9.6 out of 10, Exceptional, 35 reviews
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Country Cottage with Basketball Court/Spa/Fireplace/Enclosed Yard/Fire Pit
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, 39 reviews
"Junebug Cottage was a top notch place to stay and we enjoyed every minute of it! It is clean, well kept, and has everything needed for your stay. John is very hospitable and easy to communicate with. We loved the space and even spent some time reading on the back patio. Definitely recommend this place!"
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Spectacular Log Home Estate North Wing Apt
Property grounds
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, 25 reviews
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Property grounds
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
10.0 out of 10, Exceptional, 85 reviews
"Everything was as described, instructions to the house were precise and the facility was exactly what we 2 couples) needed for a weekend of strolls in Woodstock and trails around. We cooked 2 dinners, kitchen and BBQ were great."
The price is ￥15,550
per night
Jun 20 - Jun 21
Exquisite Mtn Chalet 5 min to Woodstock's Best Scenic Walks, we have generator.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, 63 reviews
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, 37 reviews
"it was excellent. exactly what I wanted. looking forward to coming back with family. the hot tub could have been slightly cleaner but it's like cold pizza, still good and hits the spot. honestly, a beautiful place. top notch Internet provided."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Bar (on property)
Romantic Log Cabin on Privately-Owned Lake with Fireplace
9.8 out of 10, Exceptional, 71 reviews
"The cabin is really cute & has wind chimes & garden art all around it that integrates so perfectly with the natural oasis it is set in. This is a great place for a nature loving couple to enjoy. Singing birds, frogs, turtles chipmunks & fish in the lake, are the only neighbors you will notice o this beautiful property. Karen is a lovely gracious host and both she and the cabin are very welcoming & charming. Its a perfect spot go to with your soulmate & reconnect with nature."
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Property grounds
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, 170 reviews
"What a great long weekend we had! Being on the lake, looking at the lake, bbq-ing with a view of the lake - it was all lake, all the time, which is exactly what we wanted. Plus we got perfect weather. Cabin is adorable and beds are comfortable, too."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Historic former hotel with amazing kitchen, near great hiking; great for groups!
Property grounds
Historic former hotel with amazing kitchen, near great hiking; great for groups!
10.0 out of 10, Exceptional, 36 reviews
"I was looking for somewhere that had many rooms for single and couple adults to stay at for a long weekend birthday celebration. It was super difficult to find somewhere with rooms relatively the same size and separate/private, until I came upon this listing. That was the impetus, and the reality was even better than we could have imagined. We spent most of our time in the large kitchen/dining room: cooking, eating, laughing, conversing, and playing games. At nights we would all go into large...
Historic former hotel with amazing kitchen, near great hiking; great for groups!
Hamptons on the Hudson in South Saugerties
Property grounds
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, 7 reviews
"Really cute interior. Perfect for our stay while at the horse show "
Hamptons on the Hudson in South Saugerties
Spacious restored Victorian w/ wraparound porch
Fridge, microwave, oven, stovetop
Spacious restored Victorian w/ wraparound porch
9.4 out of 10, Exceptional, 10 reviews
"Spacious house, beautiful setting. Perfect set up for a reunion with friends and family. Highlights were spending quality time on the wrap around porch and making s'mores in the fire pit. Kids loved the pool and exploring the property. Host was responsive and helpful. Highly recommend!"
Spacious restored Victorian w/ wraparound porch
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Property grounds
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, 30 reviews
"This place is wonderful!!!! It was a beautiful stay."
The price is ￥27,644
per night
Jun 18 - Jun 19
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
Property grounds
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
9.4 out of 10, Exceptional, 41 reviews
"The house is decorated beautifully, and the view of the river is great. The beds and linens were soo comfortable. Would love to return in warmer weather to enjoy the outdoors 😀"
Riverfront property in the beautiful Hudson Valley with many outdoor activities.
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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.

Other types of properties in Highland you may be interested in

Rodeway Inn & Suites New Paltz - Hudson Valley
Lobby
Rodeway Inn & Suites New Paltz - Hudson Valley
2.0 star property
7.0 out of 10, Good, 562 reviews
"No breakfast served. The room has a stale smell when I checked I requested and was granted a king size bed. "
The price is ￥11,780
per night
Jun 18 - Jun 19
Rodeway Inn & Suites New Paltz - Hudson Valley
SureStay Plus Hotel by Best Western Highland Poughkeepsie
Front of property
SureStay Plus Hotel by Best Western Highland Poughkeepsie
2.5 star property
7.6 out of 10, Good, 714 reviews
"Bed and pillows were comfortable. The lotion and soaps in bathroom were very nice. Front desk lady was down to earth and personable."
The price is ￥15,550
per night
Jul 7 - Jul 8
SureStay Plus Hotel by Best Western Highland Poughkeepsie
Best Western Plus Kingston Hotel And Conference Center
Lobby
Best Western Plus Kingston Hotel And Conference Center
2.5 star property
8.0 out of 10, Very Good, 1,001 reviews
"token machine was broken, arcade games were iffy and vending machine was out of soda. But we still had a great time in the pool and the breakfast was great and the rooms comfy and clean. Didn't know how to turn on fan in bathroom.Love the courtyard!"
The price is ￥23,409
per night
Jul 1 - Jul 2
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.

Search for holiday rentals in Highland on Expedia! You can easily find your home rentals, villas, holiday apartments in Highland using one of the methods below:

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Look no further and take a look at our great range of rental properties in Highland!

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 19 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, Apple Greens Golf Course and Franny Reese State Park 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

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

5/5 Excellent
"Property is conveniently located but in front of major road so traffic noise is I guess an avoidable. "
A verified traveler stayed at Hyatt Place Poughkeepsie / Hudson Valley
Posted 1 day ago
Hyatt Place Poughkeepsie / Hudson Valley