Westchester County Holiday Rentals

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Top cities in Westchester County

A classical fountain with columns, surrounded by a pool with a unique pattern, and cherry blossom trees in the background.
Vacation Rentals

Yonkers

Yonkers

Check prices for these dates

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

Our top choices for Westchester County holiday rentals

A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

1. Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
8.0 out of 10, Very good, (20 reviews)
"Great location"
United States
Jordan S.
The price is AU$183
includes taxes & fees
16 Nov - 17 Nov
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A kitchenette with a water dispenser, microwave, coffee machine, and snack vending machine.

2. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"Beds were adequate, nothing special but perfectly fine for a short overnight stay."
United States
Anonymous traveller
The price is AU$192
includes taxes & fees
12 Nov - 13 Nov
1 Queen Bed | Smoking
An outdoor patio with a fire pit, green chairs, and a table.

3. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
10.0 out of 10, Exceptional, (14 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is AU$448
includes taxes & fees
16 Nov - 17 Nov
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A stone staircase leading to a house with a stone wall and a metal gate.

4. 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 AU$571
includes taxes & fees
12 Nov - 13 Nov
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A modern living room with a flat-screen TV mounted on a geometric-patterned wall, a glass coffee table, a small side table with a lamp, and a wooden floor.

5. Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC

Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC
Dunwoodie
The price is AU$295
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC
A living room with a sofa, a glass coffee table, a fireplace, and a TV mounted above it.

6. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (34 reviews)
"Exactly as described, comfy and close to the Capital and restaurants. We would definitely stay here again.Directions and parking instructions were very clear and helpful."
United States
Sarah W.
The price is AU$567
includes taxes & fees
16 Nov - 17 Nov
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
A wooden deck with a white table and chairs, a glass door, and a view of green trees.

7. Newly Renovated 1BR – 5 Minutes to Valhalla Train, White Plains, WMC & NYC

Newly Renovated 1BR – 5 Minutes to Valhalla Train, White Plains, WMC & NYC
White Plains
Newly Renovated 1BR – 5 Minutes to Valhalla Train, White Plains, WMC & NYC
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

8. '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 AU$624
includes taxes & fees
19 Nov - 20 Nov
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

9. 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 AU$770
includes taxes & fees
22 Nov - 23 Nov
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A modern kitchen with white cabinets, a marble countertop, and a stainless steel range hood.

10. 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 AU$571
includes taxes & fees
23 Nov - 24 Nov
Contemporary Cozy Cottage
A modern living room with a grey sectional sofa, a round wooden coffee table, a hanging woven light fixture, and a green plant wall.

11. "Apt C " - Next to Hiking Trail - Second Floor

"Apt C " - Next to Hiking Trail - Second Floor
Northwest Yonkers
10.0 out of 10, Exceptional, (3 reviews)
"Place was very cozy and had everything we needed.Would definitely recommend!"
United States
Sandra A.
The price is AU$386
includes taxes & fees
14 Nov - 15 Nov
"Apt C " - Next to Hiking Trail - Second Floor
A covered area with exercise equipment, chairs, and a view through large windows.

12. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is AU$434
includes taxes & fees
22 Nov - 23 Nov
1BR Queen near NYC | Trails, Biking & Sauna Bliss
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

13. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AU$1,524
includes taxes & fees
16 Nov - 17 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
A compact kitchen with a refrigerator, a coffee maker, a sink, and a microwave.

14. The Subterranean Haven

The Subterranean Haven
North Side
8.8 out of 10, Excellent, (10 reviews)
"Great space but anlittle amall, the floor dips a few spots and the space is pretty tight, but perfect for a short term stay!"
United States
Hannah R.
The price is AU$386
includes taxes & fees
28 Nov - 29 Nov
The Subterranean Haven
A stone staircase leading to a viewpoint overlooking a lake, surrounded by dense greenery and trees.

15. Beautiful, spacious, and centrally located - 25 minutes from the heart of NYC.

Beautiful, spacious, and centrally located - 25 minutes from the heart of NYC.
Getty Square
9.8 out of 10, Exceptional, (16 reviews)
"Very clean and spacious apartment, close to the city and to great restaurants in Yonkers. Our host was responsive and accommodating. I would recommend renting this place."
United States
Andras M.
The price is AU$960
includes taxes & fees
12 Nov - 13 Nov
Beautiful, spacious, and centrally located - 25 minutes from the heart of NYC.
A room with a door, a lamp, a framed picture on the wall, and a small round table with items on it.

16. What's headline

What's headline
South Side
The price is AU$808
includes taxes & fees
7 Dec - 8 Dec
What's headline
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

17. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"It's an elegant older house with lots of room for company. Family friendly. The pool was great. My family enjoyed it."
United States
Karen O.
The price is AU$1,122
includes taxes & fees
16 Nov - 17 Nov
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A wooden staircase with a chandelier, leading to an upper floor. A stone wall and a flower arrangement are visible on the left.

18. 6 BR, 4 BA Mansion Close to the City

6 BR, 4 BA Mansion Close to the City
Getty Square
8.0 out of 10, Very good, (7 reviews)
"So much space to hang out with our friends!"
United States
Tamara H.
The price is AU$1,174
includes taxes & fees
12 Nov - 13 Nov
6 BR, 4 BA Mansion Close to the City
A spacious living area with a black leather sofa, a coffee table, a ceiling fan, and a blue cabinet.

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

Spacious 4-bedroom house in northern Westchester with sweeping views
Montrose
The price is AU$870
includes taxes & fees
12 Nov - 13 Nov
Spacious 4-bedroom house in northern Westchester with sweeping views
A room with a large bed, a sofa, and a patterned rug. There is a door leading to another room.

20. Cozy Spacious 2-Level Loft Venue / Birthdays, Gatherings & Celebrations

Cozy Spacious 2-Level Loft Venue / Birthdays, Gatherings & Celebrations
South Side
6.0 out of 10, (1 review)
"It’s looked very nice definitely good for parties and events however the area is a bit dangerous so staying outside can be tricky. Would open the door to people sitting and smoking at the front door as well. I enjoyed the space I was just cautious after getting a call from the host saying there was a camera still on the living area that was not made aware to me till a good 2 hours after check in. Floors could have used a nice cleanup and the furniture could be replaced from the burn marks and...
United States
Ethan P.
The price is AU$514
includes taxes & fees
12 Nov - 13 Nov
Cozy Spacious 2-Level Loft Venue / Birthdays, Gatherings & Celebrations
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 holiday rentals that suit your style

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Cottages
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Aparthotels
Aparthotels

Top Westchester County Hotel Reviews

A stone building with a tower, surrounded by a garden with large rocks and various plants.
The Abbey Inn & Spa

The Abbey Inn & Spa

The Abbey Inn & Spa
Peekskill

10/10 Excellent

.
Australia
Hannah
Reviewed September 15, 2025
The Abbey Inn & Spa

Find out more about Westchester County

Everything you need to know about Westchester County 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 Westchester County holiday rental for you. At Expedia, you can take your pick from private holiday 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 Westchester County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Westchester County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westchester County. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westchester County 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 Westchester County holiday rentals we have chosen for you start as low as AU$182 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Westchester County rentals

At Expedia, we put the best Westchester County 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 Westchester County 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 Westchester County 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 Westchester County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.