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Highland Vacation Rentals

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Vacation Rentals in Highland

Streamside Cottage Walking Distance to Town of Woodstock
Property grounds
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 13 - May 14
Streamside Cottage Walking Distance to Town of Woodstock
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, (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
Cozy Relaxing Retreat in Saugerties, NY
Property grounds
Cozy Relaxing Retreat in Saugerties, NY
10.0 out of 10, Exceptional, (28)
"I can't wait to come back, they. I loved it, It is super quiet, very stylish, huge windows to look at the trees. birds outside, very very good restaurants in a 10 minute drive. Great! "
Cozy Relaxing Retreat in Saugerties, NY
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Renovated 1850's Cottage on Storm King Mountain
Property grounds
Renovated 1850's Cottage on Storm King Mountain
10.0 out of 10, Exceptional, (7)
"Great location, very clean. Check in was easy and convenient. Will stay there again. Perfect for a family gathering."
Renovated 1850's Cottage on Storm King Mountain
Romantic Luxury Chalet With Private Pool
1 bedroom, free WiFi, bed sheets
Romantic Luxury Chalet With Private Pool
10.0 out of 10, Exceptional, (259)
"We wanted a short getaway in Woodstock NY- We found a cute Chalet with all the amenities! We have a little 7 pound fur baby- she loved it! Host located on site, but private enterance with a great security system-- it was a fully loaded studio apartment! Amazing rustic feel! Hop' Skip and a jump away from Woodstock ! The grounds are beautiful ! We will definitely be back!"
Romantic Luxury Chalet With Private Pool
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Private kitchen
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (10)
"We had a lovely weekend at this updated farm house. The house is a great combination of old comfortable farm house and updated and clean kitchens and bathrooms. We loved having Artie, the kitty, as our welcoming party."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Mid-Century DJ’s Dream
Property grounds
Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (13)
"Exactly as described. Clean & comfortable with all the amenities of home . Great for a long weekend getaway. Just a short drive from plenty of restaurants, store and attractions."
The price is $147
$217 total
includes taxes & fees
May 13 - May 14
Mid-Century DJ’s Dream
Hudson River View Suite-romantic getaway with fireplace/private deck-75 min NYC
Property grounds
Hudson River View Suite-romantic getaway with fireplace/private deck-75 min NYC
10.0 out of 10, Exceptional, (33)
"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 $80
$176 total
includes taxes & fees
May 19 - May 20
Hudson River View Suite-romantic getaway with fireplace/private deck-75 min NYC
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Exterior
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
10.0 out of 10, Exceptional, (27)
"This is our third stay in this property, and each time we had a fabulous time."
HUGE KITCHEN 4 Private Acres, 7 Min to Town, WiFi, AC, Fireplace
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
Fridge, microwave, oven, stovetop
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
10.0 out of 10, Exceptional, (27)
"Weather was not so great to be outside but the game room made up for it!"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.
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, (61)
"The property and house were beautiful, out of the way but beautiful. The fire pit, sunroom, and porch were amazing. It was great for decompressing after a West Point graduation. Thank you for sharing your little piece of heaven."
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, (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."
The price is $159
$259 total
includes taxes & fees
May 6 - May 7
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Cozy country efficiency in the Hudson Valley
Fridge, microwave, oven, stovetop
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, (37)
"This property is beautiful!! Spotless, functional and private. We absolutely loved the experience and will DEFINITELY be back again."
The price is $150
$214 total
includes taxes & fees
May 1 - May 2
Cozy country efficiency in the Hudson Valley
Hotel Woodstock - Dandelion Suite
1 bedroom, internet, bed sheets
Hotel Woodstock - Dandelion Suite
9.8 out of 10, Exceptional, (35)
"The location is perfect, especially if you’re going to a show at Colony. Nice apartment-style unit with character. Bed was comfortable. Because it’s an old building, sounds travel through the walls quite often, but a white noise app helps drown them out. Definitely not a deal breaker. Check-in/out is easy and a full kitchen is good to have if you are staying for a few days. Will definitely stay here again next time we’re in Woodstock."
The price is $99
$220 total
includes taxes & fees
May 1 - May 2
Hotel Woodstock - Dandelion Suite
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
TV, DVD player, books, video library
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
9.8 out of 10, Exceptional, (125)
"For a peaceful getaway this cottage will serve you well. It’s a long walk (15 min) to central Woodstock and also feels quiet and away from the hustle bustle. Fully equipped, cozy, quaint place. Perfect for - couple and a small pooch, if you have one. Easy communication with owners rep."
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
High Point Mtn House~April Adventure~2 hrs from NYC ULTIMATE PRIVACY!
Property grounds
High Point Mtn House~April Adventure~2 hrs from NYC ULTIMATE PRIVACY!
9.8 out of 10, Exceptional, (18)
"My recent weekend getaway to the Catskills was truly unforgettable, thanks to our wonderful host and their charming retreat nestled in the heart of this picturesque mountain region. From the moment we arrived, we were greeted with warm hospitality and a sense of tranquility that immediately set the tone for our stay. The accommodations were nothing short of perfect – cozy yet spacious, with rustic charm and modern amenities seamlessly blended together. Our host went above and beyond to ensure...
High Point Mtn House~April Adventure~2 hrs from NYC ULTIMATE PRIVACY!
Hamptons on the Hudson in South Saugerties
Property grounds
Hamptons on the Hudson in South Saugerties
9.8 out of 10, Exceptional, (6)
"Rainy but had a great time at the Wool and Sheep Festival.The fall colors were beautiful."
Hamptons on the Hudson in South Saugerties
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!
9.6 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 1 - May 2
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
The Farm at Hyde Park
Exterior
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
1 bedroom, internet, bed sheets
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 1 - May 2
Hotel Woodstock - Iris suite
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

HYATT house Fishkill/Poughkeepsie
Exterior
HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, (1001)
"The only thing about our stay at this time we did not like was the pillows. They were very old and raggedy and did not provide good support for head when sleep. The property was really clean and well kept otherwise."
The price is $128
$144 total
includes taxes & fees
May 7 - May 8
HYATT house Fishkill/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, (1000)
"It was close to the event I was attending, Staff is very polite with the exception of cleaning ladies, who started to talk loudly in am without regard to people who might be still sleeping; Room was nice , clean but the window could not be closed all the way , so had to keep the heater on all night. Overall good enough stay."
The price is $140
$157 total
includes taxes & fees
May 7 - May 8
Best Western Plus Kingston Hotel And Conference Center
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, (701)
"Very clean facilities, Staff very pleasant. "
The price is $115
$129 total
includes taxes & fees
May 1 - May 2
SureStay Plus Hotel by Best Western Highland Poughkeepsie
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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Highland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $80 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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

DoubleTree by Hilton Poughkeepsie

DoubleTree by Hilton Poughkeepsie

5/5 Excellent
"Great stay. Hotel staff was friendly. Rooms were clean and hotel is just steps away from the concert hall venue. Easy free parking. "
A verified traveler stayed at DoubleTree by Hilton Poughkeepsie
Posted 1 day ago
DoubleTree by Hilton Poughkeepsie