Westchester Holiday Rentals

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Holiday Rentals in Westchester

Condo in West Springfield

9.4 out of 10, Exceptional, (51)
"Everything we needed for a great stay and EXCELLENT communication with the host. "
United States
Matt E.
The price is AU$302
includes taxes & fees
22 Dec - 23 Dec
Beautiful 2BR/1BA Renovated Condo near DC w/pool

Apartment in West Springfield

2.0 star property
10.0 out of 10, Exceptional, (53)
"Perfect stay for a visit to the area—with all the amenities. "
United States
John B.
The price is AU$322
includes taxes & fees
15 Dec - 16 Dec
Cozy Private studio. Pet-Friendly. Conveniently located. Access 395, 495 and I95

Apartment in Springfield

9.8 out of 10, Exceptional, (12)
"Spacious, clean, lots of green space. "
United States
Siobhan G.
The price is AU$369
includes taxes & fees
6 Dec - 7 Dec
Urban Oasis I Large 2bd/1ba I Surrounded by Nature I 30 mins to DC

Apartment in Alexandria

10.0 out of 10, Exceptional, (4)
"Communication with the hosts was exceptional, along with the ease of access, and the cleanliness of the home."
United States
Natnael Y.
The price is AU$403
includes taxes & fees
21 Dec - 22 Dec
Tranquil 1-bed apt sleeps 4 overlooking Indian Creek Gorge w/ WiFi, AC & hot tub

Apartment in Triangle

10.0 out of 10, Exceptional, (12)
"Very convenient property near base. "
United States
Vicki M.
The price is AU$245
includes taxes & fees
2 Jan - 3 Jan 2026
Clean, spacious, and Cozy Basement Apartment for a memorable HomeAway experience

Holiday Home in Fairfax

9.8 out of 10, Exceptional, (21)
"Great place... "
United States
Dennis N.
The price is AU$322
includes taxes & fees
10 Dec - 11 Dec
Fairfax-GMU 2BR Retreat - Fire Pit & Wooded Views

Aparthotel in Stafford

3.0 star property
9.4 out of 10, Exceptional, (450)
"The room was very clean. It's a simple set up that afforded the opportunity to cook our own meals and save on ordering in. The General Manager was phenomenal and helpful. The rooms smelled clean and the area felt safe. Will stay again. "
United States
Kelly
Affordable Suites of America Quantico

Holiday Home in Stafford

10.0 out of 10, Exceptional, (2)
"Great place with lots of attention paid to making it comfortable and convenient."
United States
Jennifer I.
The price is AU$361
includes taxes & fees
6 Dec - 7 Dec
M&H Sweet Home is a very cozy place to relax and great area for vacation.

Holiday Home in Fairfax

10.0 out of 10, Exceptional, (35)
"Enjoyed our stay, had everything we needed. Very clean and comfortable. "
United States
Doreen B.
The price is AU$272
includes taxes & fees
7 Dec - 8 Dec
Spacious 1 BR Modern Basement Suite near GMU w/private entry - Updated Amenities

Apartment in Springfield

9.0 out of 10, Wonderful, (17)
"Incredibly kind and responsive hosts. Very peaceful location next to a pond and walking paths, close to shopping, and convenient to DC. All the amenities we needed for a lengthy stay. Would definitely stay here again."
United States
John W.
The price is AU$619
includes taxes & fees
8 Dec - 9 Dec
Lakeview - Tranquille and private suite Located 20 minutes from D.C

Condo in Annandale

8.8 out of 10, Excellent, (9)
"The location was close to my family, which I was visiting. Also not far from stores and the place was clean, which is a plus. I would stay there again when visiting."
United States
R S.
The price is AU$356
includes taxes & fees
1 Jan - 2 Jan 2026
Quiet, Remodeled 1BR/1BA Condo in Annandale, VA w/pool near DC

Holiday Home in Springfield

2.0 star property
The price is AU$170
includes taxes & fees
21 Dec - 22 Dec
Charming Retreat in the Heart of the City

Apartment in Reston

4.0 star property
9.2 out of 10, Wonderful, (7)
"The location was perfect for walking to the Metro and places to eat. It felt very safe, even walking at night. We enjoyed being so close to the Washington and Old Dominion Trail and rented bikes from a nearby Capital Bikeshare station to explore. One thing that was confusing is the check in—you need to fill out a form online with your personal details before check in. Upon arrival, press “Leasing Office” on the door pad to call the front desk to be let in. We arrived at night and were confused...
United States
Amelia
Global Luxury Suites at Town Center

Holiday Home in Woodbridge

The price is AU$553
includes taxes & fees
13 Dec - 14 Dec
Charming 2 levels guest unit in a house in amazing lake ridge area.

Holiday Home in Manassas Park

9.2 out of 10, Wonderful, (10)
"Place was clean and comfortable. It was a very nice neighborhood!"
United States
Terri G.
The price is AU$423
includes taxes & fees
1 Jan - 2 Jan 2026
A private 2BR & living area w/ patio for 4

Apartment in Reston

10.0 out of 10, Exceptional, (2)
"Clean, quiet and convenient."
United States
Liam T.
The price is AU$247
includes taxes & fees
1 Jan - 2 Jan 2026
Metro Closeby! Island Kitchen | Near Washington DC

Holiday Home in Springfield

8.0 out of 10, Very good, (1)
"The house was large with plenty of bedrooms and bathrooms. "
United States
Charles O.
The price is AU$671
includes taxes & fees
11 Dec - 12 Dec
Entertaining | 5 Bedrooms | Luxury | DC Vibe

Holiday Home in Herndon

9.2 out of 10, Wonderful, (16)
"Good stay no issues. "
United States
James C.
The price is AU$247
includes taxes & fees
17 Dec - 18 Dec
Newly Renovated Adorable Private Basement with Bathroom

Apartment in Springfield

The price is AU$463
includes taxes & fees
21 Dec - 22 Dec
In the heart of Springfield! charming and stylish retreat!

Holiday Home in Woodbridge

10.0 out of 10, Exceptional, (4)
"Great place"
United States
Kevin
The price is AU$958
includes taxes & fees
6 Dec - 7 Dec
Comfy Vacation Retreat
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 Westchester Hotel Reviews

Find out more about Westchester

Everything you need to know about Westchester 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 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Westchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westchester. 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 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 holiday rentals we have selected for you start as low as AU$194 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Westchester rentals

At Expedia, we put the best Westchester 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 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 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. 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 Westchester?

Yes, there are holiday rentals close to the most popular sights in Westchester, 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 Westchester has to offer?

Newly Renovated Adorable Private Basement with Bathroom : This holiday home rental outside of Westchester offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker. Make the most of garden in this rental home to help you unwind.

What’s there to see and do in Westchester?

While exploring the area, visit family-friendly sights like Splash Down Water Park, or get outside and enjoy nature at Lake Ridge Park, Marina and Golf Course. In the wider area, you’ll find Hylton Performing Arts Center and Westfields Golf Club.

What’s a holiday rental in Westchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Westchester. Holiday rentals feature extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family trips.