Find Vacation Homes in Town of Highlands, NY from $148

Compare and save

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Top Cities in Town of Highlands

Vacation Homes in Town of Highlands

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Fishkill
9.6 out of 10, Exceptional, (45)
"Great place for a quiet stay"
United States
Shawn M.
$295 nightly
The price is $334
Nov 30 - Dec 1
Total with taxes and fees
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Warwick
9.2 out of 10, Wonderful, (5)
"My girlfriend and I loved our stay here! We stayed for one night and it was perfect for what we needed. Very clean with easy self-check-in. The host was very responsive with all inquiries. Short walk to nice downtown area as well!"
United States
Jay D.
$133 nightly
The price is $150
Nov 24 - Nov 25
Total with taxes and fees
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

Large,Cozy,Bright Apartment, Business Themed.

Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
$585 nightly
The price is $691
Nov 24 - Nov 25
Total with taxes and fees
Large,Cozy,Bright Apartment, Business Themed.

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Newburgh
9.8 out of 10, Exceptional, (20)
"Great host, amazing area, perfect get away!"
United States
Gianna W.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Warwick
9.0 out of 10, Wonderful, (6)
"Nice to have top notch bar/restaurant downstairs!"
United States
John E
$131 nightly
The price is $148
Nov 30 - Dec 1
Total with taxes and fees
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Cozy Private Suite in a Country Home near New Paltz

2.0 star property
Wallkill
10.0 out of 10, Exceptional, (1)
"Clean, private, had no issues and the check in was easy. Had a great stay "
United States
Justin O.
Cozy Private Suite in a Country Home near New Paltz

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Newburgh
10.0 out of 10, Exceptional, (311)
"Excellent communication with great host. Pleasant, peaceful stay."
United States
Frank D.
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

Contemporary Cozy Cottage

Lake Peekskill
10.0 out of 10, Exceptional, (30)
"Very clean comfortable quiet place"
United States
Mauro C.
$367 nightly
The price is $420
Nov 24 - Nov 25
Total with taxes and fees
Contemporary Cozy Cottage

Hickory on Willow Lake

Fishkill
9.6 out of 10, Exceptional, (4)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
United States
Rachel C.
$653 nightly
The price is $744
Nov 24 - Nov 25
Total with taxes and fees
Hickory on Willow Lake

Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

Nyack
9.0 out of 10, Wonderful, (6)
"Large comfortable home in great location with multiple views of the Hudson. Our family had a pleasant stay and would definitely return to Castle in the Sky."
United States
Dr. Andrea W.
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls
10.0 out of 10, Exceptional, (4)
"Good stay, awesome place"
United States
Scott G.
$374 nightly
The price is $397
Dec 3 - Dec 4
Total with taxes and fees
House on the Babbling Brook- Quiet 2BR + King Bed!

Hudson Valley Hilltop Escape w/Hot Tub, 5private acres, near wine trail, orchard

Marlboro
10.0 out of 10, Exceptional, (5)
"Thank you for sharing your home with us. We thoroughly enjoyed our stay. The home is like a retreat - well thought out amenities & hospitality (love the dimmer switches throughout & book selections). Would definitely stay again. — WP Family "
United States
Angie W.
Hudson Valley Hilltop Escape w/Hot Tub, 5private acres, near wine trail, orchard

Majestic RiverView Estate - Breathtaking Views

Beacon
9.8 out of 10, Exceptional, (10)
"an absolutely amazing property with very responsive and lovely hosts! couldnt recommend more"
United States
Emily K.
Majestic RiverView Estate - Breathtaking Views

The Queen City Cottage

Poughkeepsie
7.4 out of 10, Good, (16)
"We had a great stay! Good location and the house was very clean. Would definitely stay here again!"
United States
Payton W.
The Queen City Cottage

Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Highland Falls
10.0 out of 10, Exceptional, (39)
"Everything was good. Heather was very attentive."
United States
Jeannette P.
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Highland
9.4 out of 10, Exceptional, (10)
"Enjoyed the stay. Nice place to relax for a weekend."
United States
Marie J.
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Stylish & Peaceful Getaway on 3 Private Acres

2.0 star property
Goshen
9.0 out of 10, Wonderful, (12)
"Great location!"
United States
Alozie E.
$438 nightly
The price is $438
Nov 24 - Nov 25
Total with taxes and fees
Stylish & Peaceful Getaway on 3 Private Acres

Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.

Greenwood Lake
9.8 out of 10, Exceptional, (8)
"Awesome place. Cozy and great communication with owners. "
United States
Dominick P.
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Carmel Hamlet
10.0 out of 10, Exceptional, (94)
"Beautiful house and property. The wild life made this stay extra special. "
United States
Jessica C.
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Fabulous 3bdrm Home w/parking!

Highland Falls
9.0 out of 10, Wonderful, (4)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
$282 nightly
The price is $310
Dec 8 - Dec 9
Total with taxes and fees
Fabulous 3bdrm Home w/parking!
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.

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Save an average of 15% on thousands of hotels when you're signed in

Top Town of Highlands Hotel Reviews

Find out more about Town of Highlands

Booking Tips to Find the Best Town of Highlands Vacation Homes


How much does it cost to rent a vacation home in Town of Highlands?

You can find incredible Town of Highlands vacation homes for all types of budgets: between $148 and $744 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Town of Highlands?

If you are looking for a great deal on your vacation home in Town of Highlands, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Town of Highlands?

There are 304 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Town of Highlands?

Begin by entering your trip dates to see what type of Town of Highlands rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Town of Highlands?

Booking Town of Highlands vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Town of Highlands rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Town of Highlands along with your vacation property, into a Town of Highlands vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

Town of Highlands Vacation Homes information

Number of reviews
620
Accommodation
304 Vacation Homes
Lowest Price
$148
Highest Price
$744

Explore a world of travel with Expedia