An aerial view of a coastal area with a clear demarcation between land and water, a sandy beach, and a distinct shoreline.

Oyster Bay Holiday Rentals

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Our top choices for Oyster Bay holiday rentals

1. Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (85 reviews)
"A beautiful home and you cannot beat the views and location!"
United States
Daniel M.
The price is AU$735
includes taxes & fees
22 Sept - 23 Sept
Captain's Cottage - Cold Spring Harbor Water Views

2. Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
The price is AU$624
includes taxes & fees
20 Sept - 21 Sept
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

3. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (178 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is AU$273
includes taxes & fees
20 Sept - 21 Sept
Stamford Suites

4. SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (10 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is AU$573
includes taxes & fees
19 Oct - 20 Oct
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

5. Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (5 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is AU$594
includes taxes & fees
28 Sept - 29 Sept
Luxe Provincial Style Studio w/ Patio & Parking

6. Huntington Village House 4BR – Walk to everything

Huntington Village House 4BR – Walk to everything
Huntington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful, clean home with plenty of space for a large family to fit comfortably. Close to plenty of restaurants and a beautiful park. The host was quick to respond to all our questions. Highly recommend booking this place."
United States
Corinne J.
The price is AU$897
includes taxes & fees
13 Oct - 14 Oct
Huntington Village House 4BR – Walk to everything

7. Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
Huntington
9.2 out of 10, Wonderful, (12 reviews)
"Great location & thoughtful amenities."
United States
Joshua
The price is AU$882
includes taxes & fees
1 Oct - 2 Oct
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

8. Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
8.8 out of 10, Excellent, (13 reviews)
"Ample on street parking - a smooth self check in - a comfortable bed and a clean bathroom in a quiet and safe walkable neighborhood. I did not know NYC could be so user friendly!"
United States
Susan O.
The price is AU$227
includes taxes & fees
21 Sept - 22 Sept
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

9. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is AU$483
includes taxes & fees
20 Sept - 21 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10. 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
9.4 out of 10, Exceptional, (52 reviews)
"This stay was very clean and easy. The check-in process was efficient. Thank you, I would definitely book again for a short stay!"
United States
Jaelyn
The price is AU$234
includes taxes & fees
21 Sept - 22 Sept
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

11. East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!
East Meadow
8.8 out of 10, Excellent, (22 reviews)
"Everything was good"
United States
Elena
The price is AU$295
includes taxes & fees
20 Sept - 21 Sept
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

12. Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (16 reviews)
"Love being able to park off the street."
United States
Joan
The price is AU$306
includes taxes & fees
21 Sept - 22 Sept
Your Perfect Getaway Between Farmingdale & Amityville

13. 2 Pvt bed Rm 1bathroom no kitchen attic

2 Pvt bed Rm 1bathroom no kitchen attic
Uniondale
9.2 out of 10, Wonderful, (9 reviews)
"Parking on the street was always available."
United States
William
The price is AU$278
includes taxes & fees
21 Sept - 22 Sept
2 Pvt bed Rm 1bathroom no kitchen attic

14. Welcoming 1 bedroom apartment in beautiful harbor village.

Welcoming 1 bedroom apartment in beautiful harbor village.
Northport
10.0 out of 10, Exceptional, (1 review)
"Beautiful clean upstairs apartment with a private entrance. Very quiet neighborhood with a small park across the street. Karen, the homeowner who lives downstairs is a wonderful person. The place was perfect for what I needed amd the location was great."
United States
Sallyann S.
The price is AU$436
includes taxes & fees
22 Sept - 23 Sept
Welcoming 1 bedroom apartment in beautiful harbor village.

15. Cozy Home.

Cozy Home.
Hempstead
9.6 out of 10, Exceptional, (5 reviews)
"Clean basement apartment, comfy couch and easy check in."
United States
Gina O.
The price is AU$382
includes taxes & fees
21 Sept - 22 Sept
Cozy Home.

16. Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Easy to get to. Listing as described. Bed and furniture are nice and comfy. Only thing I would add is a broom and dust pain and some Clorox wipes so guest can keep it neat. 5 stars! Very nice host. "
United States
Samantha
The price is AU$422
includes taxes & fees
20 Sept - 21 Sept
Sundown Escape-South Shore Long Island

17. Lofty Cozy Suite near Nassau Coliseum and Hofstra University

Lofty Cozy Suite near Nassau Coliseum and Hofstra University
Hempstead
9.0 out of 10, Wonderful, (7 reviews)
"Clean, great area, great host."
United States
Austin W.
The price is AU$357
includes taxes & fees
21 Sept - 22 Sept
Lofty Cozy Suite near Nassau Coliseum and Hofstra University

18. Julie's Cozy 2 Bedroom Basement Apartment

Julie's Cozy 2 Bedroom Basement Apartment
uniondale
10.0 out of 10, Exceptional, (5 reviews)
"Such a great place to stay! Beautiful, comfortable, clean, and the host is amazing! I will be staying here again in the future. "
United States
Heather T.
The price is AU$416
includes taxes & fees
21 Sept - 22 Sept
Julie's Cozy 2 Bedroom Basement Apartment

19. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (33 reviews)
"Exactly as described, comfy and close to the Capital and restaurants. We would definitely stay here again.Directions and parking instructions were very clear and helpful."
United States
Sarah W.
The price is AU$581
includes taxes & fees
20 Sept - 21 Sept
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

20. Cozy Studio by Hofstra University

Cozy Studio by Hofstra University
Uniondale
9.6 out of 10, Exceptional, (48 reviews)
"Great stay "
United States
Tyshieka R.
The price is AU$233
includes taxes & fees
14 Oct - 15 Oct
Cozy Studio by Hofstra University
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 favourite 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 depend 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 AU$250 per night. Entering your travel dates in the search wizard might find you 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?

1st floor 2 bedroom house with AC in Elmont NY walking distance to the UBS ARENA: This holiday home rental outside of Oyster Bay is equipped with a garden, air conditioning and WiFi to help you feel comfortable during your stay.

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 Theodore Roosevelt Memorial Park and Planting Fields Arboretum State Historic 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.