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, (82 reviews)
"We had a very good stay.. the house was very clean.. nicely decorated.. perfect for our girls trip.. the accommodations were wonderful.. town was close.. cute .. and nice to walk.. enjoyed sunsets over the water.. would definitely stay here again.."
United States
Joseph K.
The price is AU$1,077
includes taxes & fees
17 Aug - 18 Aug
Captain's Cottage - Cold Spring Harbor Water Views

2. 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$660
includes taxes & fees
3 Aug - 4 Aug
Luxe Provincial Style Studio w/ Patio & Parking

3. 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$664
includes taxes & fees
19 Aug - 20 Aug
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

4. 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)
"Had a great stay "
United States
Desiree
The price is AU$248
includes taxes & fees
5 Aug - 6 Aug
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

5. 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, (17 reviews)
"Cute little apt . Perfect location highly recommend"
United States
Kristin
The price is AU$287
includes taxes & fees
2 Aug - 3 Aug
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

6. 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, (9 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is AU$605
includes taxes & fees
2 Aug - 3 Aug
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

7. 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$310
includes taxes & fees
2 Aug - 3 Aug
Cozy Studio by Hofstra University

8. Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (10 reviews)
"Love being able to park off the street."
United States
Joan
The price is AU$324
includes taxes & fees
4 Aug - 5 Aug
Your Perfect Getaway Between Farmingdale & Amityville

9. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
7.6 out of 10, Good, (4 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is AU$208
includes taxes & fees
2 Aug - 3 Aug
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

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, (48 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$255
includes taxes & fees
1 Sept - 2 Sept
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

11. Cozy Home.

Cozy Home.
Hempstead
9.6 out of 10, Exceptional, (4 reviews)
"Clean basement apartment, comfy couch and easy check in."
United States
Gina O.
The price is AU$387
includes taxes & fees
5 Aug - 6 Aug
Cozy Home.

12. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is AU$448
includes taxes & fees
8 Aug - 9 Aug
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

13. 2 Pvt bed Rm 1bathroom no kitchen attic

2 Pvt bed Rm 1bathroom no kitchen attic
Uniondale
9.0 out of 10, Wonderful, (7 reviews)
"The overall stay was very warm & welcoming. Suitable for kids! "
United States
Tea-Anna S.
The price is AU$286
includes taxes & fees
31 Aug - 1 Sept
2 Pvt bed Rm 1bathroom no kitchen attic

14. 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, (17 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is AU$583
includes taxes & fees
9 Aug - 10 Aug
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

15. The Stone House! Pvt Entry/Sleeps 4 - by Hofstra

The Stone House! Pvt Entry/Sleeps 4 - by Hofstra
Uniondale
9.8 out of 10, Exceptional, (10 reviews)
"Our stay was wonderful! They provided coffee, water and snacks. Everything was clean and the commutation was great! We would definitely stay again!"
United States
Sarah
The price is AU$249
includes taxes & fees
5 Aug - 6 Aug
The Stone House! Pvt Entry/Sleeps 4 - by Hofstra

16. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (148 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is AU$224
includes taxes & fees
6 Aug - 7 Aug
Stamford Suites

17. 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$575
includes taxes & fees
9 Aug - 10 Aug
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

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$414
includes taxes & fees
17 Aug - 18 Aug
Julie's Cozy 2 Bedroom Basement Apartment

19. Oceanside Harbor

Oceanside Harbor
Oceanside
10.0 out of 10, Exceptional, (6 reviews)
"Clean, separated entrance. You can tell the owner put a lot of effort in to the space."
United States
Chad H.
The price is AU$387
includes taxes & fees
2 Aug - 3 Aug
Oceanside Harbor

20. 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$880
includes taxes & fees
9 Aug - 10 Aug
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
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$224 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?

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. : This holiday home rental outside of Oyster Bay has air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

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. Other popular places to visit in the area include Citi Field and Flushing Meadows-Corona Park.

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.