Photo by Wanderlust Nomad

Oyster Bay Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Oyster Bay

Holiday Home in Oyster Bay

2.0 star property
The price is NZ$2,025
includes taxes & fees
9 Dec - 10 Dec
Stunning 5BR Oasis | 3-Acre Estate & Gorg View

Mobile Home in Bay Shore

8.4 out of 10, Very good, (6)
"We wanted an inexpensive place to stay out on Long Island for July 4th weekend. We were a 15-20 minute drive to the beautiful beaches of Robert Moses and a 2 hour drive from Montauk.We were able to stay for a very reasonable price over a notoriously expensive weekend.Jenelle's communication was direct, welcoming and helpful.We would definitely stay here again!"
United States
Melanie M.
The price is NZ$371
includes taxes & fees
9 Dec - 10 Dec
Tiny Home Private, Students, Nurses, Tech

Apartment in Kings Park

2.0 star property
10.0 out of 10, Exceptional, (13)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
The price is NZ$310
includes taxes & fees
10 Dec - 11 Dec
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Aparthotel in Queens

2.5 star property
8.0 out of 10, Very good, (754)
"Yes room was very clean , quiet and staff was great."
United States
John
The price is NZ$222
includes taxes & fees
4 Jan - 5 Jan 2026
Starlight Hotel

Apartment in Central Islip

2.0 star property
8.0 out of 10, Very good, (2)
"Apt was clean and comfortable. Beds were comfortable. Area was nice. Owner communication was good. Only drawback is the plumbing situation was not advertised in the listing. Iif you are comfortable using a bidet and not flushing paper, this apt is perfect. "
United States
Deborah R.
The price is NZ$439
includes taxes & fees
9 Dec - 10 Dec
Cozy 2 bedroom retreat in long island

Apartment in Floral Park

10.0 out of 10, Exceptional, (3)
"Communication was great; all my questions were answered, which I appreciated. The place was clean and easy to get to by bus. "
United States
Vivian
The price is NZ$293
includes taxes & fees
9 Dec - 10 Dec
Charming 1-bedroom basement apartment in Floral Park with WiFi and AC

Holiday Home in Brentwood

9.4 out of 10, Exceptional, (36)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
United States
Sophie B.
The price is NZ$285
includes taxes & fees
9 Dec - 10 Dec
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Holiday Home in Inwood

2.0 star property
10.0 out of 10, Exceptional, (5)
"The property is exactly as described. It was very clean and the AC worked wonderfully which was great because the area was hot. The bed was very comfortable and overall my stay was great! I would definitely stay here again."
United States
Ryan
The price is NZ$516
includes taxes & fees
9 Dec - 10 Dec
Elegant Suite near JFK Airport

Apartment in Westport

8.8 out of 10, Excellent, (6)
"So cute and comfortable "
United States
Maria
The price is NZ$481
includes taxes & fees
10 Dec - 11 Dec
Sweet Studio w/ Lounge & Pool Table

Villa in White Plains

4.0 star property
The price is NZ$1,178
includes taxes & fees
9 Dec - 10 Dec
Luxury NYC Home with Free Parking for 12

Aparthotel in Norwalk

3.5 star property
8.4 out of 10, Very good, (40)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is NZ$533
includes taxes & fees
18 Dec - 19 Dec
Guesthouse at Norwalk Inn

Holiday Home in Elmont

9.4 out of 10, Exceptional, (45)
"Nice and cozy place Farida is very nice. Thank you "
Canada
Jeremy
The price is NZ$385
includes taxes & fees
9 Dec - 10 Dec
It's a Loft on the Second floor. Mins away from UBS Arena, JFK Airport

Apartment in Elmont

9.8 out of 10, Exceptional, (18)
"This was a great place to stay if attending an event at the USB Arena, was there to see Grace Potter and Chris Stapleton. Was an easy walk back to the place without dealing with parking lot traffic. Would definitely stay again for any other event. Place was clean and had everything we needed, would recommend! "
United States
Rachel
The price is NZ$570
includes taxes & fees
9 Dec - 10 Dec
Luxury Studio Suite. Walking distance to UBS Arena

Apartment in Huntington Station

10.0 out of 10, Exceptional, (17)
"Place was clean, decorated adorably and well stocked with essentials- even a coffee bar! Communication was also very good. Would definitely recommend! "
United States
natalie m.
The price is NZ$843
includes taxes & fees
20 Dec - 21 Dec
THE OASIS @ LONG ISLAND

Apartment in East Meadow

10.0 out of 10, Exceptional, (11)
"Very easy check in process, great communication with host, close to so many venues and the beach is just a short drive away!!"
United States
Joanne P.
The price is NZ$276
includes taxes & fees
11 Dec - 12 Dec
Zen Oasis - Pvt. Entry Studio Bed+Bath by NUMC

Apartment in North Baldwin

9.8 out of 10, Exceptional, (60)
"Great little place. Verbelle was an excellent host, and the apartment was very nicely set up. When we return to Long Island we would definitely stay there again. "
United States
Joe T.
The price is NZ$560
includes taxes & fees
9 Dec - 10 Dec
Relax and rejuvenate in this Hideaway Apartment close to public transportation .

Apartment in Freeport

7.6 out of 10, Good, (14)
"Great stay "
United States
Lindsay
The price is NZ$426
includes taxes & fees
9 Dec - 10 Dec
Cozy Freeport Retreat / 8 min Loffs Lake / Pets 🐶

Holiday Home in Cold Spring Harbor

10.0 out of 10, Exceptional, (73)
"Location was perfect!"
United States
Linda J P.
The price is NZ$813
includes taxes & fees
9 Dec - 10 Dec
Captain's Cottage - Cold Spring Harbor Water Views

Holiday Home in Hempstead

2.0 star property
The price is NZ$362
includes taxes & fees
14 Dec - 15 Dec
Julie's Cozy Haven -Peaceful 1BR Retreat

Apartment in Hempstead

8.4 out of 10, Very good, (7)
"Clean"
United States
Alvin
The price is NZ$419
includes taxes & fees
4 Jan - 5 Jan 2026
Lunavista Cozy Studio
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Oyster Bay Hotel Reviews

Find out more about Oyster Bay

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

Oyster Bay holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oyster Bay. 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 Oyster Bay 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 Oyster Bay holiday rentals we have selected for you start as low as NZ$222 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oyster Bay rentals

At Expedia, we put the best Oyster Bay 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 Oyster Bay 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 Oyster Bay 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 Oyster Bay. 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

Can I find a holiday rental in Oyster Bay?

Yes, there are holiday rentals in Oyster Bay close to Planting Fields Arboretum State Historic Park, or you can select a more secluded option if you're looking for a relaxing stay. Oyster Bay is known for its shopping and restaurants.

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

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside of Oyster Bay is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Oyster Bay?

Expedia has 4 holiday rentals for your stay in Oyster Bay.

What’s there to see and do in Oyster Bay?

Cultural attractions include Sagamore Hill National Historic Site and 20th Century Cycles, whereas Planting Fields Arboretum State Historic Park and Theodore Roosevelt Memorial Park are a couple of picturesque spots to enjoy the outdoors. Theodore Roosevelt Sanctuary and Audubon Center and Beekman Beach are other places to visit while you're in town.

What’s a holiday rental in Oyster Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oyster Bay. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for family trips or small group gatherings.