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Cortlandt Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Cortlandt vacation rentals

A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

1. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (95 reviews)
"The host, Maria, was excellent in staying in touch and personally met me upon check-in and checkout. The location is very convenient for walking around downtown or easily drive to nearby outings."
United States
Margaret S.
The price is CA $267
CA $508 total
includes taxes & fees
Nov 18 - Nov 19
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

2. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (9 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is CA $320
CA $579 total
includes taxes & fees
Nov 19 - Nov 20
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A stone staircase leading to a house with a stone wall and a metal gate.

3. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (28 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is CA $357
CA $576 total
includes taxes & fees
Nov 15 - Nov 16
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Living area

4. Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
8.4 out of 10, Very good, (5 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is CA $156
CA $285 total
includes taxes & fees
Dec 8 - Dec 9
Cozy 1-bedroom retreat minutes from West Point!
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

5. Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (43 reviews)
"We’ve actually stayed here twice so that should tell you we enjoy the space and the host is lovely."
United States
Heather M.
The price is CA $321
CA $571 total
includes taxes & fees
Nov 22 - Nov 23
Contemporary Cozy Cottage
A house with a view of a bridge and mountains.

6. Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (150 reviews)
"We had a great stay!!"
United States
Jasmine
The price is CA $282
CA $433 total
includes taxes & fees
Nov 16 - Nov 17
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Step up to a warm welcome - our charming entryway, complete with a hanging birdhouse, sets the tone for a peaceful stay.

7. Walk-to-Lake Cottage With Grill for Peaceful Fall Days

Walk-to-Lake Cottage With Grill for Peaceful Fall Days
Putnam Valley
9.8 out of 10, Exceptional, (25 reviews)
"Absolute comfortable stay. Everything you need and fantastic host!! Will be back."
United States
Lisa
The price is CA $301
CA $748 total
includes taxes & fees
Nov 15 - Nov 16
Walk-to-Lake Cottage With Grill for Peaceful Fall Days
A spacious living area with a black leather sofa, a coffee table, a ceiling fan, and a blue cabinet.

8. Spacious 4-bedroom house in northern Westchester with sweeping views

Spacious 4-bedroom house in northern Westchester with sweeping views
Montrose
The price is CA $706
CA $837 total
includes taxes & fees
Nov 15 - Nov 16
Spacious 4-bedroom house in northern Westchester with sweeping views
A modern kitchen with stainless steel appliances, wooden cabinets, and a contemporary light fixture.

9. 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, (7 reviews)
"Location was perfect for West Point visit. The space was clean and recently updated, the beds very comfortable, and perfect layout and spacious for 3-4 people. The host was welcoming and responsive."
United States
Maria L.
The price is CA $264
CA $442 total
includes taxes & fees
Nov 17 - Nov 18
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
A blue house with a white porch, a welcome sign, and a mailbox.

10. 3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.4 out of 10, Very good, (7 reviews)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
3BR West Point Retreat-3min to Back Gate+ King Bed
A wooden coffee table with two decorative planters in a living room.

11. Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (26 reviews)
"Clean, modern, functional, comfortable. Great stay"
United States
Jerell T.
The price is CA $292
CA $475 total
includes taxes & fees
Dec 15 - Dec 16
Walk to WP Gate + Free Parking!
A modern kitchen with stainless steel appliances, white cabinetry, a coffee station, and a dining area with a wooden table and bench.

12. Local Artist Inspired | Walk to WestPoint + King Bed

Local Artist Inspired | Walk to WestPoint + King Bed
Highland Falls
9.6 out of 10, Exceptional, (21 reviews)
"Great location! Easy checkin, checkout process. We would stay again"
United States
Morgan S.
The price is CA $179
CA $594 total
includes taxes & fees
Nov 15 - Nov 16
Local Artist Inspired | Walk to WestPoint + King Bed
A hallway with a wooden door, a black table with a sign, and large green plants.

13. 3BR Near West Point | Coffee Bar | Sleeps 6

3BR Near West Point | Coffee Bar | Sleeps 6
Highland Falls
9.6 out of 10, Exceptional, (4 reviews)
"Clean and convenient near West Point golf course"
United States
mario b.
The price is CA $168
CA $581 total
includes taxes & fees
Nov 15 - Nov 16
3BR Near West Point | Coffee Bar | Sleeps 6
A covered area with exercise equipment, chairs, and a view through large windows.

14. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is CA $361
CA $434 total
includes taxes & fees
Nov 15 - Nov 16
1BR Queen near NYC | Trails, Biking & Sauna Bliss
A living room with a wooden floor, a black sofa, a coffee table, and a ceiling fan.

15. Perfect 2BR with Free Parking! Walk to West Point!

Perfect 2BR with Free Parking! Walk to West Point!
Highland Falls
The price is CA $286
CA $484 total
includes taxes & fees
Nov 30 - Dec 1
Perfect 2BR with Free Parking! Walk to West Point!
A room with a wooden floor, a white door with a number, and a window with blinds.

16. Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is CA $282
CA $508 total
includes taxes & fees
Dec 15 - Dec 16
Lovely 3BR Home with parking-Walk to WP Gate!
A dining area with a table, chairs, a vase with flowers, a hanging light fixture, and wall decorations.

17. Mountain-View 2BR Steps from Thayer Gate

Mountain-View 2BR Steps from Thayer Gate
Highland Falls
The price is CA $257
CA $450 total
includes taxes & fees
Nov 15 - Nov 16
Mountain-View 2BR Steps from Thayer Gate
A house with a white front door, a small porch with a white railing, and a window with a green curtain.

18. Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (12 reviews)
"House was exactly as described. Would stay again."
United States
Beth M.
The price is CA $300
CA $518 total
includes taxes & fees
Dec 15 - Dec 16
Fabulous 3bdrm Home w/parking!
A wooden deck with a table and chairs, overlooking a lake with cherry blossoms and autumn foliage.

19. Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms

Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
Lake Peekskill
8.0 out of 10, Very good, (3 reviews)
"This home was just as advertised and perfect for a girls weekend getaway. It was clean, cozy and a picture-perfect fall view. Would highly recommend."
United States
Karen W.
The price is CA $473
CA $892 total
includes taxes & fees
Nov 16 - Nov 17
Lakefront Escape • Sauna • 1 Hr from NYC• 3 spacious bedrooms
A brick building with a sign reading 'Lobby' in front.

20. 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
Dec 5 - Dec 6
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
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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Find vacation rentals that suit your style

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Top Cortlandt Hotel Reviews

A buffet with various food items, including omelets and baked goods, served in metal containers.
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
Peekskill

10/10 Excellent

We enjoyed our stay very much. It was lovely.
Canada
Blair
Reviewed November 6, 2025
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Find out more about Cortlandt

Everything you need to know about Cortlandt 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 Cortlandt 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 Cortlandt vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cortlandt vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cortlandt. 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 Cortlandt 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 Cortlandt vacation rentals we have selected for you start as low as CA $151 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cortlandt rentals

At Expedia, we put the best Cortlandt 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 Cortlandt 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 Cortlandt 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 Cortlandt. 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 Cortlandt?

Yes, we offer vacation rentals near well known sights in Cortlandt, or you can go with a more remote option if you want a relaxing place to stay.

What's the top vacation rental in Cortlandt?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: Visitors like this Cortlandt vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Cortlandt?

With 3 Expedia vacation rentals, you're sure to find just the right place for your Cortlandt stay.

What’s there to see and do in Cortlandt?

Hudson Highlands State Park and Blue Mountain Reservation are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Monteverde at Oldstone and Regal UA Cortlandt Town Center.

What are vacation rentals like in Cortlandt?

Vacation rentals are private accommodations you can stay in for a couple days or more in Cortlandt. Vacation rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.