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Oyster Bay Holiday Rentals

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Our top choices for Oyster Bay holiday rentals

Bright & Comfortable Home in the Heart of It All

Bright & Comfortable Home in the Heart of It All
Central Islip
10.0 out of 10, Exceptional, (1 review)
"The host was very helpful and amazing. He also assisted us with transportation due to a mishap with our car rental. However if you want a peaceful and relaxing trip in Long Island please book this place. Reggie is an amazing guy .Thank you for hosting us"
United States
Lakisha M.
The price is NZ$675
includes taxes & fees
24 June - 25 June
Bright & Comfortable Home in the Heart of It All

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is NZ$418
includes taxes & fees
15 June - 16 June
Spacious 3BR Family Home Near Everything

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 NZ$522
includes taxes & fees
29 June - 30 June
Sundown Escape-South Shore Long Island

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, (43 reviews)
"This place was the perfect location for us. Almost exact center between Jones beach and Port Jefferson. Clean and identical to what is shown."
United States
Marcus
The price is NZ$264
includes taxes & fees
16 June - 17 June
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Tiny Home Private, Students, Nurses, Tech

Tiny Home Private, Students, Nurses, Tech
Bay Shore
7.8 out of 10, Good, (8 reviews)
"Great host, nice place."
United States
Brian C.
The price is NZ$562
includes taxes & fees
21 June - 22 June
Tiny Home Private, Students, Nurses, Tech

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (21 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is NZ$301
includes taxes & fees
17 June - 18 June
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Lakefront GetawaY & Romantic NightS + BeacheS NeaR

Lakefront GetawaY & Romantic NightS + BeacheS NeaR
West Islip
10.0 out of 10, Exceptional, (3 reviews)
"The entire experience was amazing. The grounds and living space were exceptional.Our host was extremely helpful and accommodating. Will definitely boom again in the future."
United States
Melissa G.
The price is NZ$472
includes taxes & fees
23 June - 24 June
Lakefront GetawaY & Romantic NightS + BeacheS NeaR

1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.8 out of 10, Excellent, (22 reviews)
"Well suited for our needs."
United States
Teresa D.
The price is NZ$321
includes taxes & fees
11 June - 12 June
1 bedroom 1 bath private entrance

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Commack
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay"
United States
Kenneth B.
The price is NZ$1,671
includes taxes & fees
15 June - 16 June
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

World Cup Rental Waterfront Beach House Sunsets Private 90 mins MetLife

World Cup Rental Waterfront Beach House Sunsets Private 90 mins MetLife
Northport
9.4 out of 10, Exceptional, (16 reviews)
"Great host and property!"
United States
Anonymous traveller
World Cup Rental Waterfront Beach House Sunsets Private 90 mins MetLife

Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (6 reviews)
"The whole experience was great"
United States
David
The price is NZ$391
includes taxes & fees
16 June - 17 June
Your Perfect Getaway Between Farmingdale & Amityville

4 BR. 2 BTH, HOT TUB, MINS TO JONES BEACH, MINS TO RIVIERA WALK TO TRAIN TO NYC

4 BR. 2 BTH, HOT TUB, MINS TO JONES BEACH, MINS TO RIVIERA WALK TO TRAIN TO NYC
Massapequa
10.0 out of 10, Exceptional, (12 reviews)
"Lovely property. Comfortable. Great outdoor space "
United States
Ari P.
The price is NZ$5,148
includes taxes & fees
1 July - 2 July
4 BR. 2 BTH, HOT TUB, MINS TO JONES BEACH, MINS TO RIVIERA WALK TO TRAIN TO NYC

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, (7 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is NZ$637
includes taxes & fees
23 June - 24 June
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 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 NZ$667
includes taxes & fees
15 June - 16 June
Luxe Provincial Style Studio w/ Patio & Parking

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is NZ$591
includes taxes & fees
8 July - 9 July
Spacious Studio with Pool Table

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 NZ$679
includes taxes & fees
15 June - 16 June
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Huntington
9.6 out of 10, Exceptional, (8 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is NZ$389
includes taxes & fees
25 June - 26 June
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Lovely RV with AC in charming Bethpage a mile from the train to NYC

Lovely RV with AC in charming Bethpage a mile from the train to NYC
Bethpage
7.0 out of 10, Good, (4 reviews)
"Super convenient and the host was very responsive. I highly recommend."
United States
Andrew B.
The price is NZ$400
includes taxes & fees
11 June - 12 June
Lovely RV with AC in charming Bethpage a mile from the train to NYC

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, (78 reviews)
"A true port in the storm"
United States
Trey S.
The price is NZ$1,007
includes taxes & fees
15 June - 16 June
Captain's Cottage - Cold Spring Harbor Water Views

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is NZ$647
includes taxes & fees
6 July - 7 July
Guesthouse at Norwalk Inn
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$264 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?

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. : This holiday home rental outside of Oyster Bay has air conditioning and WiFi 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.