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Holiday Rentals in Shirley

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Holiday Rentals in Shirley

Our top choices for Shirley holiday rentals

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is €551
includes taxes & fees
1 Sept - 2 Sept
Modern Vacation home. Close to The Hamptons

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

9.8 out of 10, Exceptional, (20)
"Great costal location on Long Island. Eddie is a rockstar and took great care of us. Very unique architecture with lots of cool angles. Awesome family gettaway...!"
The price is €566
includes taxes & fees
9 Sept - 10 Sept
3 Story Beach Waterview, 3 KING bed, golf putting green!

Relaxing Smith Point Beach House on private canal

9.6 out of 10, Exceptional, (58)
"Great location, so close to the beach! We very much enjoyed our time at the property, had everything we could need. The hosts were amazing!"
Relaxing Smith Point Beach House on private canal

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

9.4 out of 10, Exceptional, (25)
"its small but very nice for a short stay would recommend."
The price is €146
includes taxes & fees
27 Aug - 28 Aug
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

10.0 out of 10, Exceptional, (2)
"Friendly host, very good location and a simple check-in process. Few minutes drive to the beach. "
The price is €316
includes taxes & fees
2 Sept - 3 Sept
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (66)
"Very nice place for a family to stay"
The price is €1,104
includes taxes & fees
1 Sept - 2 Sept
Newly Renovated Luxury Beach House Ocean Bay Park

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (133)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

10 Bedroom Hampton House with a regulation size Pickleball court

9.8 out of 10, Exceptional, (30)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball court

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (33)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Walk to Beach 2BR Near Dining & Shopping

6.4 out of 10, (19)
"The beach is private and you need to be a Brookhaven resident to be admitted. This is not specified anywhere on the listing. Communication about this with the owner via app was rather poor. "
The price is €267
includes taxes & fees
2 Sept - 3 Sept
Walk to Beach 2BR Near Dining & Shopping

East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

10.0 out of 10, Exceptional, (96)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is €541
includes taxes & fees
1 Sept - 2 Sept
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters

10.0 out of 10, Exceptional, (58)
"From the moment we booked this trip we knew we were in for a treat. Windows on the Sea did not disappoint! From the early communication with our hosts and their thoughtful check-ins leading up to our trip, this was the best experience we could ask for. We highly recommend staying here!"
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

9.4 out of 10, Exceptional, (71)
"A gorgeous home! We pretended to be in the Great Gatsby. Lovely pool and grounds. We loved tennis...who knew? That was a surprise hit. Very spacious "
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (12)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!

Weekends, midweeks and full weeks available! Steps to Beach, town and ferries!

9.8 out of 10, Exceptional, (21)
"Great time...close to the beach or the bay"
Weekends, midweeks and full weeks available! Steps to Beach, town and ferries!

Spacious Home Located Close to Stony Brook!

6.8 out of 10, (18)
"Great stay great people great costumer care definitely reccomend"
Spacious Home Located Close to Stony Brook!

NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room

9.2 out of 10, Wonderful, (14)
"Beautiful property! Well stocked with essentials and perfect for our group with and age range o16 - 83"
NEW 7 Bedrm House-Pool, Swim-Up Bar, Grill, Pool Table, Fitness and play room

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
9.0 out of 10, Wonderful, (4)
"Large open first floor for a large family stay. Great back patio with a nice view of the river. Don't miss the morning swans. "
The price is €794
includes taxes & fees
1 Sept - 2 Sept
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

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

Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

10.0 out of 10, Exceptional, (2)
"Everything was as pictured, and the whole place was very clean. It was a perfect stay for us, and we will come again soon!"
The price is €148
includes taxes & fees
3 Sept - 4 Sept
Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach
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 Shirley Hotel Reviews

Find out more about Shirley

Find out more about Shirley

Everything you need to know about Shirley 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 Shirley holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Shirley holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shirley holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shirley. 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 Shirley 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 Shirley holiday rentals we have selected for you start as low as €146 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shirley rentals

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

Yes, there are holiday rentals close to the most popular sights in Shirley, or you can select a more secluded option if you're looking for a relaxing stay. Shirley is known for its parks.

What are some of the best holiday rentals that Shirley has to offer?

Modern Vacation home. Close to The Hamptons: This highly rated holiday home rental in Shirley is located on the waterfront, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Shirley?

With 18 Expedia holiday rentals, you're guaranteed to find just the right place for your Shirley stay.

What can I see and do in Shirley?

Great South Bay and Carmans River are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Lasorda Legacy Park and TWA Flight 800 International Memorial.

What are holiday rentals like in Shirley?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shirley. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.