Photo by Karen Wirtz

Search Highland Cottage Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Highland

Luxe Family Home on Orange Lake w/ Private Dock!
Interior

Luxe Family Home on Orange Lake w/ Private Dock!

3.0 star property
Luxe Family Home on Orange Lake w/ Private Dock!
Charming Gardiner Home w/ Yard & Sunroom
Interior

Charming Gardiner Home w/ Yard & Sunroom

3.0 star property
10.0 out of 10, Exceptional, (1)
Charming Gardiner Home w/ Yard & Sunroom
Bright Cornwall-on-hudson Vacation Rental!
Interior

Bright Cornwall-on-hudson Vacation Rental!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
Bright Cornwall-on-hudson Vacation Rental!
Pet-friendly Hopewell Junction Home w/ Pool
Outdoor dining

Pet-friendly Hopewell Junction Home w/ Pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house was so incredible. Not only was it in a quiet nice neighborhood the inside was incredible too. Pool table as well as a pool it was perfect for my stay to have fun and enjoy our time. They were very communicative and welcoming to their house. Everything was comfortable and clean. Can’t say any bad things about this place. Definitely going to book again. I already miss it. "
Pet-friendly Hopewell Junction Home w/ Pool
Charming Cottage w/ Yard - 2 Mi to Tinker St!
Interior

Charming Cottage w/ Yard - 2 Mi to Tinker St!

3.0 star property
Charming Cottage w/ Yard - 2 Mi to Tinker St!
Charming Victorian Retreat w/ Hudson River Views
Interior

Charming Victorian Retreat w/ Hudson River Views

3.0 star property
Charming Victorian Retreat w/ Hudson River Views
Historic 1800s Cornwall-on-hudson Cottage!
Interior

Historic 1800s Cornwall-on-hudson Cottage!

3.0 star property
Historic 1800s Cornwall-on-hudson Cottage!
Quaint Woodstock Escape - 2 Mi to Tinker St!
Interior

Quaint Woodstock Escape - 2 Mi to Tinker St!

3.0 star property
Quaint Woodstock Escape - 2 Mi to Tinker St!
Peaceful Hurley Retreat ~ 1 Mi to Main Street
Interior

Peaceful Hurley Retreat ~ 1 Mi to Main Street

3.0 star property
Peaceful Hurley Retreat ~ 1 Mi to Main Street
Waterfront Wallkill Duplex Home w/ Fire Pits!
Interior

Waterfront Wallkill Duplex Home w/ Fire Pits!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great for my kids and family for options to play outdoors and indoors games together. Loved the coffee bar and the details in the bathrooms with all the little things we could use down to the qtips and things. Really great for our family trip memories!!"
Waterfront Wallkill Duplex Home w/ Fire Pits!
Fire Pit + On-site Pond: Hudson Valley Home!
Interior

Fire Pit + On-site Pond: Hudson Valley Home!

3.0 star property
Fire Pit + On-site Pond: Hudson Valley Home!
Eclectic Ulster County Cabin w/ Private Hot Tub
Interior

Eclectic Ulster County Cabin w/ Private Hot Tub

3.0 star property
10.0 out of 10, Exceptional, (1)
"Was nice and secluded and felt very intimate"
Eclectic Ulster County Cabin w/ Private Hot Tub
Charcoal Chalet by Avantstay A+ Design w/ Firepit
Interior

Charcoal Chalet by Avantstay A+ Design w/ Firepit

3.0 star property
Charcoal Chalet by Avantstay A+ Design w/ Firepit
Updated Home w/ Patio Half Mile to West Point
Interior

Updated Home w/ Patio Half Mile to West Point

3.0 star property
Updated Home w/ Patio Half Mile to West Point
Dreamy Hudson Valley Cottage w/ State Park Views
Interior

Dreamy Hudson Valley Cottage w/ State Park Views

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was amazing with great amenities. The kitchen was stocked with all the utensils and cutlery. The patio was a good addition. Overall great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views
Saugerties Farmhouse: Sauna & Countryside Views
Interior

Saugerties Farmhouse: Sauna & Countryside Views

3.0 star property
10.0 out of 10, Exceptional, (1)
"My stay here was short—just three nights—but it was absolutely perfect. The house is beautiful and comfortable, equipped with everything I needed to feel welcome. I particularly loved the heated floor in the bathroom and the cozy ambiance throughout the entire house. My favorite part was sitting on the porch, enjoying coffee and watching the birds. I definitely plan to return for another stay. The house was easy to find and impeccably clean. Communication was seamless, and the instructions were...
Saugerties Farmhouse: Sauna & Countryside Views
Woodstock Getaway w/ Hot Tub ~ 2 Mi to Dtwn!
Interior

Woodstock Getaway w/ Hot Tub ~ 2 Mi to Dtwn!

3.0 star property
Woodstock Getaway w/ Hot Tub ~ 2 Mi to Dtwn!
Updated/pet-friendly Cabin By Hikes and Woodstock!
Interior

Updated/pet-friendly Cabin By Hikes and Woodstock!

3.0 star property
8.0 out of 10, Very good, (1)
"This is a lovely small cottage in the middle of a forest. It has two bedrooms upstairs and bathroom downstairs. There was not enough linens and no bathroom appliances. "
Updated/pet-friendly Cabin By Hikes and Woodstock!
Kingston Home < 2 Mi to Bluestone Wild Forest
Interior

Kingston Home < 2 Mi to Bluestone Wild Forest

3.0 star property
6.0 out of 10, (1)
"No lighted house numbers, so an evening check in was difficult. Attempted to get more blankets, and our texts were unanswered for a 3 night stay. "
Kingston Home < 2 Mi to Bluestone Wild Forest
Hudson Valley Horse Farm Retreat in Salt Point
Front of property

Hudson Valley Horse Farm Retreat in Salt Point

3.0 star property
8.0 out of 10, Very good, (1)
Hudson Valley Horse Farm Retreat in Salt Point
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Highland Hotel Reviews

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"Very comfortable all around. I will stop here each time I pass through Fishkill!!! "
Mary J. 1-night trip
Posted 2 days ago
Quality Inn & Suites Fishkill South near I-84

Frequently asked questions

Why book your cottage in Highland with Expedia?
We think that vacays should be a walk in the park, so if you're in search of cottages in Highland at an affordable price, Expedia is here to help. Save cash and choose a cheap option far from the hustle and bustle, or book a 5-star cottage to pamper your loved ones.
How can I find cheap cottages in Highland?
Expedia can help you easily source cheap cottages in Highland. To book a superb stay in a few clicks, try out the filter tool to tailor your search results by budget, amenities and star rating.
What is there to do in Highland near my cottage?
Once you've unpacked your bags, head out and discover the wonderful things Highland has to offer. Apple Greens Golf Course is a top attraction to add to your must-see list.