Vacation Rentals in Town of Highlands

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Top Cities in Town of Highlands

Top Vacation Rentals in Town of Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (122)
"It has an incredible mountain and water view. "
$272 nightly
The price is $308
Sep 3 - Sep 4
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

9.8 out of 10, Exceptional, (29)
"Great place for a quiet stay"
$294 nightly
The price is $333
Sep 21 - Sep 22
Total with taxes and fees
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

9.8 out of 10, Exceptional, (12)
"The place was wonderful! Even before check-in, Don was very communicative and made sure to ask about our preferences for one of the rooms.We had a fantastic stay — the home was very spacious, and the layout was perfect for a large family.The highlight for us was the beautiful lake view. We loved the outdoor seating area right by the water — perfect for relaxing with a coffee in the morning or unwinding in the evening. The kayaks were a great bonus and made for some fun time on the lake.We will...
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

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

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

10.0 out of 10, Exceptional, (66)
"The yard and river are so beautiful. It’s a wonderful place to stay!"
$185 nightly
The price is $207
Sep 3 - Sep 4
Total with taxes and fees
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

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

10.0 out of 10, Exceptional, (306)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

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

10.0 out of 10, Exceptional, (6)
Ann Creek: Charming 2 BR fully renovated house at Greenwood Lake. Dog friendly.

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

9.2 out of 10, Wonderful, (10)
"We were visiting with friends from the UK and we had a very comfortable stay. Everything we needed, very clean, easy to find and very quiet neighborhood. Would highly recommend."
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

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

10.0 out of 10, Exceptional, (87)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (19)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
$481 nightly
The price is $544
Sep 15 - Sep 16
Total with taxes and fees
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

9.8 out of 10, Exceptional, (7)
"Patrick and Katherine are excellent hosts with an incredible property in an amazing location. We had such an incredible time. The carriage house is so comfortable and welcoming. I absolutely loved just sitting on the balcony enjoying the beautiful view, birds, and my coffee. This was my first time using Vrbo, (glad to have found an alternative to another site I no longer support). Wow, I have been missing out!! The stocked fridge was such a lovely surprise. Everything was just fantastic. Our...
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

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.

A luxurious stay.

6.0 out of 10, (2)
"If you want to go to a diagusting neighborhood then this is your place. We felt so unsafe we didn’t even stay there. We got a hotel. It is that bad. As nice as the inside is, the outside and neighborhood will have you running. Music blasting stinks of weed homeless people all over. Do not book this place. The owner didn’t even refund us our cleaning fee. Trust me STAY AWAY."
$251 nightly
The price is $284
Sep 12 - Sep 13
Total with taxes and fees
A luxurious stay.

Large,Cozy,Bright Apartment, Business Themed.

8.8 out of 10, Excellent, (15)
"Very cozy stay with responsive host"
$552 nightly
The price is $652
Sep 3 - Sep 4
Total with taxes and fees
Large,Cozy,Bright Apartment, Business Themed.

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
$369 nightly
The price is $419
Sep 15 - Sep 16
Total with taxes and fees
Rustic Cabin in Fishkill!

Cabin in the Heart of the Hudson Valley, Cabin 1

9.8 out of 10, Exceptional, (28)
"Really a nice place. Great for an overnight stop in the Hudson Valley"
$202 nightly
The price is $239
Sep 3 - Sep 4
Total with taxes and fees
Cabin in the Heart of the Hudson Valley, Cabin 1

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

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

3.0 star property
10.0 out of 10, Exceptional, (2)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
$263 nightly
The price is $285
Sep 4 - Sep 5
Total with taxes and fees
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cabin in the heart of the Hudson Valley, Cabin 2

9.6 out of 10, Exceptional, (22)
"Perfect for a getaway weekend for my wife and I! Easy check-in, clean, and although it's off a busy road, we found it peaceful and quiet. Would definitely stay again!"
$149 nightly
The price is $176
Sep 7 - Sep 8
Total with taxes and fees
Cabin in the heart of the Hudson Valley, Cabin 2

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

10.0 out of 10, Exceptional, (191)
"We loved the house, it was very quiet, the view of the lake was beautiful (even though it was rainy and cloudy). The decoration was really nice and it felt super cozy. The host was also very responsive. "
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
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

Find out more about Town of Highlands

Find out more about Town of Highlands

Discover your perfect Town of Highlands vacation rental with Expedia

How many vacation rentals are available in Town of Highlands?


Expedia has plenty of vacation rentals to choose from in and around  Town of Highlands, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Town of Highlands?


The selection of Town of Highlands vacation rentals we have selected for you start as low as $176 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Town of Highlands?


Vacation rentals in Town of Highlands come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Town of Highlands vacation rentals to suit everyone. 


Why should I choose a vacation rental in Town of Highlands?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Town of Highlands vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Town of Highlands?


Find vacation rentals in Town of Highlands by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Town of Highlands.  


What amenities are available in a vacation rental in Town of Highlands?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Town of Highlands vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Town of Highlands?   


Everytime is a great time to head to Town of Highlands! Staying in a Town of Highlands vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Town of Highlands. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Town of Highlands vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Town of Highlands, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Town of Highlands vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.