Oyster Bay Holiday Rentals

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Our top choices for Oyster Bay holiday rentals

The price is NZ$2,032
includes taxes & fees
16 Mar - 17 Mar
Stunning 5BR Oasis | 3-Acre Estate & Gorg View
8.6 out of 10, Excellent, (7 reviews)
"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$350
includes taxes & fees
16 Mar - 17 Mar
Tiny Home Private, Students, Nurses, Tech
9.4 out of 10, Exceptional, (39 reviews)
"We had a good experience and we brought our little pup and she was welcome there. Clean and quiet stay "
United States
janice s.
The price is NZ$286
includes taxes & fees
16 Mar - 17 Mar
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is NZ$464
includes taxes & fees
23 Mar - 24 Mar
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
10.0 out of 10, Exceptional, (18 reviews)
"Perfect spot for a quick trip"
United States
James P.
The price is NZ$306
includes taxes & fees
17 Mar - 18 Mar
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is NZ$548
includes taxes & fees
11 Mar - 12 Mar
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
7.6 out of 10, Good, (14 reviews)
"Great stay "
United States
Lindsay
The price is NZ$435
includes taxes & fees
8 Apr - 9 Apr
Cozy Freeport Retreat / 8 min Loffs Lake / Pets 🐶

Apartment in Freeport

Nautical Elegance
9.2 out of 10, Wonderful, (9 reviews)
"Great place to stay. Host was great and had amazing communication. "
United States
Maggie I.
The price is NZ$322
includes taxes & fees
17 Mar - 18 Mar
Nautical Elegance

Holiday Home in Hempstead

Grandiosely Pleasant Suite 2
8.0 out of 10, Very good, (12 reviews)
"Great place to stay! The host was very responsive. The place was clean, and lots of safe parking! "
United States
Lorraine S.
The price is NZ$412
includes taxes & fees
23 Mar - 24 Mar
Grandiosely Pleasant Suite 2

Holiday Home in Uniondale

Cozy Studio by Hofstra University
9.6 out of 10, Exceptional, (38 reviews)
"great stay. The only real inconvenience was the lack of paper plates but other than that everything was perfect."
United States
Jayceon
The price is NZ$282
includes taxes & fees
28 Mar - 29 Mar
Cozy Studio by Hofstra University

Holiday Home in Inwood

Elegant Suite near JFK Airport
10.0 out of 10, Exceptional, (5 reviews)
"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$424
includes taxes & fees
23 Mar - 24 Mar
Elegant Suite near JFK Airport

Holiday Home in Hempstead

Majestically Pleasant Suite
8.0 out of 10, Very good, (3 reviews)
"Great small place to chill, very clean, and cozy definitely recommend "
United States
Patryck H.
The price is NZ$412
includes taxes & fees
23 Mar - 24 Mar
Majestically Pleasant Suite
9.8 out of 10, Exceptional, (6 reviews)
"Perfect for a weekend getaway "
United States
Naika C.
The price is NZ$420
includes taxes & fees
23 Mar - 24 Mar
Sophisticated Suite Near JFK Airport
8.2 out of 10, Very good, (18 reviews)
"Great location"
United States
Jordan S.
The price is NZ$227
includes taxes & fees
14 Mar - 15 Mar
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
7.4 out of 10, Good, (3 reviews)
"We had a great experience staying at this cozy apartment in Hempstead, NY. The neighborhood felt safe and quiet, with plenty of street parking available—very convenient. The apartment was clean, well-kept, and just the right size for two people. Check-in was seamless, and the host was very responsive and helpful. It’s a perfect spot for anyone visiting Hofstra University or the surrounding area. Would definitely stay here again!"
United States
Lori K.
The price is NZ$412
includes taxes & fees
23 Mar - 24 Mar
Lofty Cozy Suite near Nassau Coliseum and Hofstra University
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is NZ$529
includes taxes & fees
16 Mar - 17 Mar
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Holiday Home in Hempstead

Cozy Cottage
The price is NZ$435
includes taxes & fees
23 Mar - 24 Mar
Cozy Cottage

Apartment in Hempstead

Lunavista Cozy Studio
8.4 out of 10, Very good, (7 reviews)
"Clean"
United States
Alvin
Lunavista Cozy Studio
9.2 out of 10, Wonderful, (9 reviews)
"This stay was private and comfortable. Checking in was easy with an electronic lock and the host was very communicative with my questions. 2 things to note are that the walls are thin between this unit and the main house so you can indistinctly hear each other, and the mattress is quite hard, but I know some people prefer that. The bathroom is modern and clean and overall everything was easy. "
United States
Zoe P.
The price is NZ$274
includes taxes & fees
14 Mar - 15 Mar
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
9.8 out of 10, Exceptional, (20 reviews)
"We stayed for 2 nights for an Islanders game and this was the perfect spot! Great walking distance, super clean, and great amenities!! Didn’t have too many questions for the host because everything was laid out nicely, but they were responsive when I did! I would highly recommend!! "
United States
Emma H.
The price is NZ$543
includes taxes & fees
11 Mar - 12 Mar
Luxury Studio Suite. Walking distance to UBS Arena
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 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$201 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?

Peaceful Gathering Modern Kitchen & Living space, Huge discounts are available: This holiday home rental outside of Oyster Bay offers a selection of games, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 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 Oyster Bay?

Expedia has 3 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 Center Island 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.