Hillside Lake Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Hillside Lake vacation rentals

Terrace/patio

Vacation Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is ￥11,727
￥51,235 total
includes taxes & fees
Jan 26 - Jan 27
House on the Babbling Brook- Quiet 2BR + King Bed!
Fridge, oven, stovetop, coffee/tea maker

Apartment in Highland Falls

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is ￥11,885
￥39,242 total
includes taxes & fees
Jan 26 - Jan 27
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Property grounds

Apartment in Staatsburg

Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (44 reviews)
"Great host and excellent accommodations! "
United States
Elaine L.
The price is ￥17,709
￥31,149 total
includes taxes & fees
Jan 25 - Jan 26
Mid-Century DJ’s Dream
3 bedrooms, desk, iron/ironing board, travel crib

Apartment in Highland Falls

Local Artist Inspired | Walk to WestPoint + King Bed
9.4 out of 10, Exceptional, (11 reviews)
"Great place to stay if you have a West Point student - super close to all West Point related activities. The place itself needs some work but it’s functional."
United States
Jesse C.
The price is ￥14,104
￥58,742 total
includes taxes & fees
Jan 25 - Jan 26
Local Artist Inspired | Walk to WestPoint + King Bed
Exterior detail

Apartment in Beacon

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
9.8 out of 10, Exceptional, (43 reviews)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is ￥17,432
￥37,036 total
includes taxes & fees
Jan 25 - Jan 26
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Property grounds

Apartment in Hyde Park

Hudson Valley Farm Getaway- West/Llama Lover Lane
9.8 out of 10, Exceptional, (6 reviews)
"Perfect little apartment on an amazing farm property...thanks for having us and look forward to returning! "
United States
ADRIENNE
The price is ￥25,276
￥32,987 total
includes taxes & fees
Jan 25 - Jan 26
Hudson Valley Farm Getaway- West/Llama Lover Lane
Dining

Apartment in Beacon

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
10.0 out of 10, Exceptional, (32 reviews)
"Great time and great place to stay "
United States
S S.
The price is ￥18,383
￥39,407 total
includes taxes & fees
Feb 10 - Feb 11
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Property grounds

Cabin in Carmel

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
10.0 out of 10, Exceptional, (3 reviews)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Property grounds

Apartment in Dover Plains

Hoppy Hill Farm House
9.6 out of 10, Exceptional, (4 reviews)
"The cabin was perfect. Had everything we needed and clear directions. "
United States
Jocelyn L.
The price is ￥15,847
￥30,656 total
includes taxes & fees
Jan 26 - Jan 27
Hoppy Hill Farm House
Smart TV, fireplace, books

Apartment in Kent

Mid Century Modern Studio w/ Full Kitchen - Newly Built
9.8 out of 10, Exceptional, (10 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥30,902
￥39,499 total
includes taxes & fees
Jan 25 - Jan 26
Mid Century Modern Studio w/ Full Kitchen - Newly Built
1 bedroom, free WiFi, bed sheets

Camping in New Milford

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
8.0 out of 10, Very Good, (1 review)
"We camped at Freedom Farm and enjoyed the secluded woods setting for our tent. Everything was clean and well prepared for our stay, and the hosts were friendly and helpful. It is beautifully situated and is a short drive from some excellent hiking and biking in nearby state parks. I think a couple of things, though, could be improved. The tent was set up on an incline, which made sleeping a bit less comfortable than it might have been. I would recommend that the hosts build a level platform...
United States
Eric
The price is ￥23,771
￥30,506 total
includes taxes & fees
Jan 24 - Jan 25
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
1 bedroom, free WiFi, bed sheets

Camping in New Milford

Creekside Retreat Tent
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely beautiful location and wonderful hosts very romantic spot lots of hiking trails near and on premises me and my husband loved the fact we slept by the water and can hear the water running all night very peaceful and beautiful site ."
United States
yarelis t.
The price is ￥23,771
￥30,506 total
includes taxes & fees
Jan 24 - Jan 25
Creekside Retreat Tent
Fridge, microwave, oven, stovetop

Vacation Home in Holmes

"Country outside the city " 3 bedrooms 2 full bathrooms
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
The price is ￥31,948
￥91,357 total
includes taxes & fees
Jan 26 - Jan 27
"Country outside the city " 3 bedrooms 2 full bathrooms
TV, fireplace

Vacation Home in Carmel Hamlet

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
9.8 out of 10, Exceptional, (12 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is ￥26,385
￥56,073 total
includes taxes & fees
Jan 25 - Jan 26
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
3 bedrooms, desk, iron/ironing board, free WiFi

Vacation Home in Highland Falls

Sleek Escape: Modern 3 BR- 4 Min from West Point !
10.0 out of 10, Exceptional, (3 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is ￥20,760
￥70,134 total
includes taxes & fees
Feb 10 - Feb 11
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Smart TV, fireplace

Apartment in Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
The price is ￥19,967
￥30,656 total
includes taxes & fees
Jan 25 - Jan 26
Private, Cozy, Clean apartment in lovely Hyde Park
Living area

Apartment in Brewster

The Hideaway
10.0 out of 10, Exceptional, (6 reviews)
"I will definitely stay there when I come up north again. The accommodations were very comfortable and well supplied. As an added bonus with a wonderful cats that came around for loving"
United States
Cindy S.
The price is ￥24,563
￥50,150 total
includes taxes & fees
Jan 26 - Jan 27
The Hideaway
Terrace/patio

Apartment in Highland

Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
10.0 out of 10, Exceptional, (1 review)
"Everyone was just right! The home is perfect for a photo shoot. We weren't there for that, but we thought the setting was unique and beautiful! Everything we needed!!"
United States
Rebecca D.
The price is ￥26,148
￥60,523 total
includes taxes & fees
Jan 24 - Jan 25
Step into history & unwind at Spring apt a charming 🏡 at the❤️of NYHudson Valley
Property grounds

Vacation Home in Highland Falls

3BR West Point Retreat-3min to Back Gate+ King Bed
8.0 out of 10, Very Good, (6 reviews)
"Wonderful stay! The property is within walking distance of the little downtown area & had driveway parking. It was clean & plenty spacious. Property owners had great communication! This is a property with 2 units, but we were not bothered by any extra noise. "
United States
Waylon J.
The price is ￥17,432
￥65,794 total
includes taxes & fees
Feb 4 - Feb 5
3BR West Point Retreat-3min to Back Gate+ King Bed
Outdoor dining

Cabin in Newburgh

Cabin in the heart of the Hudson Valley, Cabin 4
9.0 out of 10, Wonderful, (26 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is ￥20,443
￥31,637 total
includes taxes & fees
Jan 25 - Jan 26
Cabin in the heart of the Hudson Valley, Cabin 4
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hillside Lake Hotel Reviews

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Everything was great . "
Jason 1-night trip
Posted 1 day ago
Hampton Inn & Suites Poughkeepsie

Find out more about Hillside Lake

Search for holiday rentals in Hillside Lake on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillside Lake using one of the methods below:

  • View our selection of featured holiday rentals in Hillside Lake
  • Use the map to find apartments and other holiday homes in the Hillside Lake neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hillside Lake while they last

Look no further and take a look at our great range of rental properties in Hillside Lake!

Frequently asked questions

Are there vacation rentals in Hillside Lake?

Yes, you can find vacation rentals close to top sights in Hillside Lake, or you can select a secluded option if you're looking for relaxation.

What are some of the best vacation rentals that Hillside Lake has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: Visitors like this Hillside Lake vacation home rental. It offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and an electric kettle, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Hillside Lake?

Explore the area and family-friendly sights such as SplashDown Beach, or get out into nature at a spot like Walkway Over the Hudson State Historic Park. Stormville Airport Antique Show & Flea Market and Poughkeepsie Galleria are a couple of places you'll find in the larger area.

What’s a vacation rental in Hillside Lake like?

Vacation rentals are private properties where you can stay for short or long periods in Hillside Lake. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for families.