Vacation Rentals in Town of Highlands

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Top Vacation Rentals in Town of Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Stroll through a serene residential setting surrounded by a lush lawn, a tree, and a picturesque bridge.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (118)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is ￥27,533
￥44,567 total
includes taxes & fees
Jul 29 - Jul 30
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Discover Nature’s Glory! Perfect Family Home
Stroll up to the charming two-story house surrounded by lush greenery and a serene atmosphere.

Discover Nature’s Glory! Perfect Family Home

10.0 out of 10, Exceptional, (1)
"Wonderful location to amazing hikes and West Point. "
Discover Nature’s Glory! Perfect Family Home
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Relax on the serene deck, surrounded by bare trees and a frozen lake.

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

10.0 out of 10, Exceptional, (299)
"Beautiful, quiet property that was a great getaway from the city. A pair of bald eagles were circling the lake which was a really amazing surprise! "
The price is ￥65,756
￥88,227 total
includes taxes & fees
Aug 10 - Aug 11
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Relax in a hot tub with a serene lake and forest view.

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (16)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is ￥42,837
￥92,527 total
includes taxes & fees
Jul 28 - Jul 29
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Relax in this serene outdoor seating area with a covered patio overlooking a lush garden.

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

9.8 out of 10, Exceptional, (26)
"Plenty of room for my family"
The price is ￥40,274
￥52,021 total
includes taxes & fees
Jul 29 - Jul 30
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Terrace/patio

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

9.8 out of 10, Exceptional, (7)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Charming Inn Steps away from Downtown Warwick only an Hour away from NYC
Step into the grand lobby, featuring a stunning staircase, reception desk with a lighted panel, and elegant artwork on the walls.

Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

9.0 out of 10, Wonderful, (4)
"I stayed here for the weekend to hike a small section of the AT. It was perfect for my trip. "
The price is ￥11,203
￥21,787 total
includes taxes & fees
Jul 28 - Jul 29
Charming Inn Steps away from Downtown Warwick only an Hour away from NYC
Magnificent Lake View
Property grounds

Magnificent Lake View

2.0 star property
Magnificent Lake View
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and ample counter space.

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

10.0 out of 10, Exceptional, (84)
"The house was super clean and very easy to take care of while we were here. It was perfect for a remote getaway, hiking and just being quiet. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Relax in a hot tub surrounded by lush greenery and a wooden deck.

New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

10.0 out of 10, Exceptional, (25)
"A beautiful and bright cottage in a serene but convenient location. It was thoughtfully set up for a family getaway and was exceptionally clean. My entire family enjoyed the stay!"
The price is ￥87,724
￥139,560 total
includes taxes & fees
Jul 27 - Jul 28
New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Indoor Pool Paradise | 6BR + Huge Decks
Enjoy dining or socializing on this covered deck with a table and chairs, surrounded by a serene landscape.

Indoor Pool Paradise | 6BR + Huge Decks

The price is ￥132,526
￥263,982 total
includes taxes & fees
Jul 28 - Jul 29
Indoor Pool Paradise | 6BR + Huge Decks
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Relax on the covered porch with comfortable seating and a small table, perfect for casual dining or unwinding.

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

9.8 out of 10, Exceptional, (6)
"Really liked that each room had it's own temperature control"
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Cozy Cabin with Sauna & Firepit!
Enjoy a peaceful retreat on this serene property with a covered patio, perfect for relaxing with a seating area and umbrella.

Cozy Cabin with Sauna & Firepit!

9.2 out of 10, Wonderful, (33)
"Excellent "
Cozy Cabin with Sauna & Firepit!
Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA
Enjoy meals in this elegant dining area with a glass-top table, white chairs, and a beautiful painting of cranes.

Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA

8.8 out of 10, Excellent, (5)
"Had a wonderful, relaxing stay here. Convenient location allowed us to walk everywhere we wanted to go!"
Apartment with Expansive Views; River & Mountains Walk to Train, Main St, DIA
Hickory on Willow Lake
Escape to a serene oasis beneath a triangular gazebo, surrounded by lush greenery and a tranquil hillside setting.

Hickory on Willow Lake

9.4 out of 10, Exceptional, (3)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is ￥62,241
￥90,384 total
includes taxes & fees
Aug 4 - Aug 5
Hickory on Willow Lake
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Fridge, microwave, oven, stovetop

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

8.0 out of 10, Very Good, (1)
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Simply Unforgettable HotTub, Pool, Pets, <1 Hr NYC
Interior

Simply Unforgettable HotTub, Pool, Pets, <1 Hr NYC

10.0 out of 10, Exceptional, (77)
"Lovely stay at large and clean home with great kitchen and pool area. Lots of room for everyone and attentive hosts"
Simply Unforgettable HotTub, Pool, Pets, <1 Hr NYC
Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train
Enjoy a tranquil retreat on the rooftop patio, surrounded by lush greenery and a garden.

Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train

9.4 out of 10, Exceptional, (3)
"We only stayed a couple days, but the location is quaint and apartment newly refurnished. The owner was very helpful and great to work with. Highly recommend!"
Ideal Location 1block to Main St. Restaurants , Bars,Hudson River, Bus/ Train
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.
Situated on a sloped terrain, this charming house features a prominent turret and balcony, surrounded by a beautifully maintained garden with various shrubs and flowering plants.

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

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."
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.
Modern penthouse suite in a restored grain tower with private roof deck.
Surrounded by lush greenery, this charming building features a central chimney and a flat roof.

Modern penthouse suite in a restored grain tower with private roof deck.

10.0 out of 10, Exceptional, (22)
"Wonderful stay!"
The price is ￥49,427
￥79,111 total
includes taxes & fees
Jul 26 - Jul 27
Modern penthouse suite in a restored grain tower with private roof deck.
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.
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Top Town of Highlands Hotel Reviews

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

10/10 Excellent
"I liked the room and the surrounding area!"
Michael 1-night trip
Posted 1 day ago
Courtyard by Marriott Middletown Goshen