Holiday Rentals in Hillside Lake

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Our top choices for Hillside Lake holiday rentals

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

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is €281
includes taxes & fees
4 Feb - 5 Feb
House on the Babbling Brook- Quiet 2BR + King Bed!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (16 reviews)
"Great Unit."
United States
Rudy R.
The price is €223
includes taxes & fees
4 Feb - 5 Feb
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
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 €353
includes taxes & fees
4 Feb - 5 Feb
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is €238
includes taxes & fees
4 Feb - 5 Feb
Charming 1-bedroom apartment in Carmel with WiFi, AC

Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (44 reviews)
"Great host and excellent accommodations! "
United States
Elaine L.
The price is €168
includes taxes & fees
5 Feb - 6 Feb
Mid-Century DJ’s Dream

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
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 €166
includes taxes & fees
25 Feb - 26 Feb
Hoppy Hill Farm House

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen
Beacon
10.0 out of 10, Exceptional, (32 reviews)
"Great time and great place to stay "
United States
S S.
The price is €214
includes taxes & fees
4 Feb - 5 Feb
Luxe Studio 2 on Main Street- Luxury Steam Shower, Kitchen

Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.4 out of 10, Exceptional, (31 reviews)
"A very cute, convenient, and affordable stay with timely, friendly communication from the owner. Our dog loved it and we appreciated the ability to have a private place to stay."
United States
Sara B.
The price is €172
includes taxes & fees
4 Feb - 5 Feb
Cabin in the heart of the Hudson Valley, Cabin 2

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Highland Falls
10.0 out of 10, Exceptional, (5 reviews)
"Very nice property. We have a son at West Point and approximately an hour from New York City. Host was quick to respond to questions and provided excellent information. We will stay here again. "
United States
Mark V.
The price is €237
includes taxes & fees
4 Feb - 5 Feb
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking

Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
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 €331
includes taxes & fees
4 Feb - 5 Feb
Local Artist Inspired | Walk to WestPoint + King Bed

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
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 €315
includes taxes & fees
24 Feb - 25 Feb
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
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 €366
includes taxes & fees
4 Feb - 5 Feb
3BR West Point Retreat-3min to Back Gate+ King Bed

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (43 reviews)
"Adorable place to stay in an adorable town! "
United States
Mary L.
The price is €202
includes taxes & fees
4 Feb - 5 Feb
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.0 out of 10, Wonderful, (4 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is €301
includes taxes & fees
4 Mar - 5 Mar
Fabulous 3bdrm Home w/parking!

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is €215
includes taxes & fees
5 Feb - 6 Feb
Mid Century Modern Studio w/ Full Kitchen - Newly Built

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.0 out of 10, Wonderful, (10 reviews)
"We had a great last minute visit to Hopewell Junction and enjoyed a lovely stay at the chapel! It’s a very unique experience and quiet and peaceful. We enjoyed the bbq and an evening fire with smores! "
United States
Esther P.
The price is €220
includes taxes & fees
4 Feb - 5 Feb
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake
New Fairfield
10.0 out of 10, Exceptional, (18 reviews)
"Great location and condition. Roome enough for everyone."
United States
Christopher H.
The price is €413
includes taxes & fees
8 Feb - 9 Feb
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm
New Milford
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 €166
includes taxes & fees
4 Feb - 5 Feb
Secluded Mountaintop Retreat – Rustic Luxury & Panoramic Views at Freedom Farm

Creekside Retreat Tent

Creekside Retreat Tent
New Milford
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 €167
includes taxes & fees
4 Feb - 5 Feb
Creekside Retreat Tent

"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
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 €487
includes taxes & fees
4 Feb - 5 Feb
"Country outside the city " 3 bedrooms 2 full bathrooms
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 Hillside Lake Hotel Reviews

Find out more about Hillside Lake

Everything you need to know about Hillside Lake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hillside Lake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillside Lake holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hillside Lake holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillside Lake. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillside Lake holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillside Lake holiday rentals we have selected for you start as low as €172 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hillside Lake rentals

At Expedia, we put the best Hillside Lake holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hillside Lake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillside Lake holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillside Lake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Hillside Lake?

Yes, there are holiday rentals close to the most popular sights in Hillside Lake, or you can select a more secluded option if you're looking for a relaxing stay.

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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This holiday home rental outside of Hillside Lake 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 that 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 wider area.

What’s a holiday rental in Hillside Lake like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillside Lake. Holiday rentals feature amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for family trips.