Hillside Lake Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Hillside Lake vacation rentals

A brick building with a sign reading 'Lobby' in front.

1. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.0 out of 10, Wonderful, (21 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is CA $111
CA $128 total
includes taxes & fees
Nov 25 - Nov 26
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

2. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is CA $100
CA $113 total
includes taxes & fees
Nov 23 - Nov 24
1 King Bed | Non-Smoking, Kitchen, Shower
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

3. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is CA $237
CA $377 total
includes taxes & fees
Nov 8 - Nov 9
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
A brick building with a sign reading 'Lobby' in front.

4. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.0 out of 10, Wonderful, (22 reviews)
"great place tostay"
United States
Anonymous traveller
The price is CA $122
CA $141 total
includes taxes & fees
Nov 24 - Nov 25
2 Full Beds | Non-Smoking, Kitchen
A small blue house with two blue Adirondack chairs, a small table, and a potted plant.

5. Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.6 out of 10, Exceptional, (41 reviews)
"This was a great place to stay with our cats for a night on our way to Vermont."
United States
George J.
The price is CA $208
CA $312 total
includes taxes & fees
Dec 3 - Dec 4
Cabin in the heart of the Hudson Valley, Cabin 2
A two-story house with a balcony, surrounded by lush greenery.

6. Quiet Solitude with Firepit, Electric Stove & Private Deck

Quiet Solitude with Firepit, Electric Stove & Private Deck
Hopewell Junction
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Sara's place. Unfortunately due to all the rain we couldn't enjoy the outside facilities. The bedroom loft is charming and everything you need is there. Thanks for a great stay!"
United States
stephanie a.
Quiet Solitude with Firepit, Electric Stove & Private Deck
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

7. Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (36 reviews)
"Great place! Nicely decorated with attention to detail. My wife and I would stay again if we are back in the area."
United States
Tim G.
The price is CA $236
CA $386 total
includes taxes & fees
Dec 3 - Dec 4
Cabin in the Heart of the Hudson Valley, Cabin 1
A brick building with a sign reading 'Lobby' in front.

8. 1 Queen Bed | Non-Smoking, Kitchen

1 Queen Bed | Non-Smoking, Kitchen
Fishkill
7.8 out of 10, Good, (26 reviews)
"The property was clean and pet friendly. However, the small extended stay room with a kitchen had no glasses or bowls or flat ware. You can't expect any additional accomodations beyond the room."
United States
Ray
The price is CA $111
CA $128 total
includes taxes & fees
Nov 25 - Nov 26
1 Queen Bed | Non-Smoking, Kitchen
Floor plan

9. 1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen

1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen
Fishkill
9.0 out of 10, Wonderful, (18 reviews)
"Good so far"
United States
Anonymous traveller
The price is CA $111
CA $126 total
includes taxes & fees
Nov 22 - Nov 23
1 Queen Bed | ADA/RI Shower/Nsmk/Kitchen
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is CA $172
CA $424 total
includes taxes & fees
Nov 9 - Nov 10
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A rural landscape with a barn, a silo, and a bridge with rocks and purple flowers in the foreground.

11. A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail

A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
Wallkill
9.2 out of 10, Wonderful, (20 reviews)
"The room was super cute and clean. It had everything that I needed."
United States
Carrie
The price is CA $101
CA $187 total
includes taxes & fees
Nov 8 - Nov 9
A Cozy Private Suite Near New Paltz: Farms, Nature, Hiking & Bike the rail trail
A living room with a fireplace, a painting, shelves with decorative items, and a television.

12. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (53 reviews)
"Beautiful little apartment, walking to shops and easy parking"
United States
Martha Z.
The price is CA $278
CA $504 total
includes taxes & fees
Nov 8 - Nov 9
Grant - A Tranquil One Bedroom Steps from River
A cozy living room with a sofa, a dining table, and a bed.

13. Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (75 reviews)
"Lovely cottage in a beautiful setting with everything you need to rest, relax, and enjoy this lovely part of New York state. Highly recommend!"
United States
Frances N.
The price is CA $259
CA $475 total
includes taxes & fees
Dec 3 - Dec 4
Cozy country efficiency in the Hudson Valley
A deck with wicker furniture and a view of a lake and mountains.

14. Private River View Deck · Walk Downtown

Private River View Deck · Walk Downtown
Newburgh
10.0 out of 10, Exceptional, (1 review)
The price is CA $199
CA $581 total
includes taxes & fees
Nov 12 - Nov 13
Private River View Deck · Walk Downtown
A modern kitchen with white cabinets, a central island, and a view to the outside.

15. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (13 reviews)
"We thoroughly enjoyed our stay. We would definitely come back! A fantastic location. And very good communication with the host, Alexander."
United States
elizabeth
The price is CA $160
CA $281 total
includes taxes & fees
Nov 10 - Nov 11
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

16. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean rooms, Diner down the block, family friendly, communication was prompt and clear"
United States
Joseph
The price is CA $352
CA $507 total
includes taxes & fees
Nov 13 - Nov 14
Rustic Cabin in Fishkill!
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

17. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (31 reviews)
"Everything was just as it was in our past stays. The place was clean, neat and organized very well. Communication with the host was very easy and almost immediate reply."
United States
Albert
The price is CA $208
CA $312 total
includes taxes & fees
Dec 3 - Dec 4
Cabin in the heart of the Hudson Valley, Cabin 4
Bedroom

18. 2 Full Beds | Non-Smoking, Micfridge

2 Full Beds | Non-Smoking, Micfridge
Fishkill
10.0 out of 10, Exceptional, (2 reviews)
"Checked out local spots nearby, easy parking available."
United States
Anonymous traveller
The price is CA $172
CA $194 total
includes taxes & fees
Nov 15 - Nov 16
2 Full Beds | Non-Smoking, Micfridge
A modern kitchen with a granite countertop, a built-in stove, and a dining area with a glass table and chairs.

19. Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful property with ample space for parking. Host was super nice and met all of our needs!"
United States
Nicole Y.
The price is CA $301
CA $678 total
includes taxes & fees
Nov 9 - Nov 10
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
A living room with a fireplace, two armchairs, a sofa, and a TV.

20. Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (26 reviews)
"Very private, rural spot. Immaculate, thoughtfully furnished, lacking nothing"
United States
benjamin
The price is CA $208
CA $257 total
includes taxes & fees
Nov 10 - Nov 11
Mid Century Modern Studio w/ Full Kitchen - Newly Built
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

A modern hotel with a prominent 'Hyatt Place' sign, outdoor seating area, and a covered entrance.
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley
Crown Heights

10/10 Excellent

Loved it. Big rooms. Comfy beds.
Canada
Jodi
Reviewed September 16, 2026
Hyatt Place Poughkeepsie / Hudson Valley

Find out more about Hillside Lake

Everything you need to know about Hillside Lake vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillside Lake vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hillside Lake vacation 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 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.  The selection of Hillside Lake vacation rentals we have selected for you start as low as CA $520 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 vacation 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 vacation.

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 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?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: Visitors like this Hillside Lake vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, 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 Bowdoin 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.