Book Holiday Homes in Shirley

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Shirley

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Brentwood NY
The price is AU$241 per night from 17 May to 18 May
AU$241
17 May - 18 May
includes taxes & fees
Located in Brentwood, this vacation home is within a 5-minute drive of Hauppauge Industrial Park and Nissequogue River.
Opens in a new windowCozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Ocean Beach NY
With a stay at this vacation home in Bay Shore, you'll be a 2-minute walk from Great South Bay and 15 minutes by foot from Ocean Beach.
Opens in a new windowSpacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park
Spacious Home Located Close to Stony Brook!

Spacious Home Located Close to Stony Brook!

Lake Grove NY
With a stay at this vacation home in Lake Grove, you'll be within a 10-minute drive of Stony Brook University and Smithaven Mall.
Opens in a new windowSpacious Home Located Close to Stony Brook!
Save an average of 15% on thousands of hotels when you're signed in
Lakeside Hideaway

Lakeside Hideaway

Lake Ronkonkoma NY
With a stay at this vacation home in Ronkonkoma, you'll be within a 15-minute drive of Stony Brook University and Lake Ronkonkoma.
Opens in a new windowLakeside Hideaway
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly

Westhampton Beach NY
With a stay at this vacation home in Westhampton Beach, you'll be by the sea, within a 5-minute drive of The Hamptons Beaches and The Great Lawn.
Opens in a new windowWHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly
Near the Hamptons - Private Pool, Jacuzzi Retreat

Near the Hamptons - Private Pool, Jacuzzi Retreat

Calverton NY
With a stay at this vacation home in Calverton, you'll be within a 10-minute drive of Splish Splash Water Park and Out East Family Fun.
Opens in a new windowNear the Hamptons - Private Pool, Jacuzzi Retreat
Cozy beach hose minutes from Hamptons

Cozy beach hose minutes from Hamptons

Calverton NY
The price is AU$1,278 per night from 18 May to 19 May
AU$1,278
18 May - 19 May
includes taxes & fees
With a stay at this vacation home in Calverton, you'll be within a 10-minute drive of Splish Splash Water Park and Wildwood State Park.
Opens in a new windowCozy beach hose minutes from Hamptons
Charming Riverhead home with large outdoor patio & backyard  firepit

Charming Riverhead home with large outdoor patio & backyard firepit

Riverhead NY
With a stay at this vacation home, you'll be centrally located in Riverhead, within a 10-minute drive of Splish Splash Water Park and All Star Bowling.
Opens in a new windowCharming Riverhead home with large outdoor patio & backyard firepit
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Centereach NY
With a stay at this vacation home in Centereach, you'll be within a 5-minute drive of Stony Brook University and Smithaven Mall.
Opens in a new windowCozy 4-bedroom house with AC and WiFi in Centereach, New York.
Don't see what you're looking for?
See all available properties in Shirley
View all properties
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.

Shirley Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Shirley vacation homes are the perfect way for you to wing it.

Holiday houses in Shirley let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Shirley in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Shirley adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Shirley with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Shirley vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Shirley Holiday Homes essential information

Accommodation
709 Holiday Homes
Lowest Price
AU$143
Highest Price
AU$1,278
Popular accommodation
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. , Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park, Spacious Home Located Close to Stony Brook!, Lakeside Hideaway, WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool,Beach,Fam/Pet Frly, Near the Hamptons - Private Pool, Jacuzzi Retreat, Cozy beach hose minutes from Hamptons, Charming Riverhead home with large outdoor patio & backyard firepit, Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Top trending hotels in Shirley

3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!

Shirley NY
With a stay at this vacation home in Shirley, you'll be by the sea, a 4-minute walk from Great South Bay and a 3-minute drive from Smith Point County Park.
Opens in a new window3 Story Beach Waterview, 3 KING bed, golf putting green!
Hyatt Regency Long Island

Hyatt Regency Long Island

4 out of 5
1717 Motor Parkway Hauppauge NY
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 25 May to 26 May
AU$199
25 May - 26 May
includes taxes & fees
Located in Hauppauge, Hyatt Regency Long Island is by the ocean, within a 5-minute drive of Hauppauge Industrial Park and Lakeland County Park.
Opens in a new windowHyatt Regency Long Island
Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

3 out of 5
3845 Veterans Memorial Hwy Ronkonkoma NY
Fully refundableReserve now, pay when you stay
The price is AU$143 per night from 21 May to 22 May
AU$143
21 May - 22 May
includes taxes & fees
When you stay at Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport in Ronkonkoma, you'll be near the airport, within a 5-minute drive of Bohemia ...
Opens in a new windowClarion Hotel & Conference Center Ronkonkoma MacArthur Airport
Save an average of 15% on thousands of hotels when you're signed in
Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

3.5 out of 5
2000 North Ocean Ave. Farmingville NY
Fully refundableReserve now, pay when you stay
The price is AU$179 per night from 17 May to 18 May
AU$179
17 May - 18 May
includes taxes & fees
Located in Farmingville, Hampton Inn Long Island-Brookhaven is connected to a shopping center, within a 10-minute drive of Holtsville Ecology Site and Animal ...
Opens in a new windowHampton Inn Long Island-Brookhaven
Don't see what you're looking for?
See all available properties in Shirley
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.