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Our top choices for Oyster Bay holiday rentals

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is £194
includes taxes & fees
20 May - 21 May
Spacious 3BR Family Home Near Everything

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 £282
includes taxes & fees
18 May - 19 May
Guesthouse at Norwalk Inn

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 £458
includes taxes & fees
25 May - 26 May
Sundown Escape-South Shore Long Island

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.6 out of 10, (115 reviews)
"I stay there because it's fully equipped to cook and parking is excellent."
United States
fatima
The price is £128
includes taxes & fees
21 May - 22 May
Stamford Suites

Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
The price is £412
includes taxes & fees
29 May - 30 May
Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
The price is £449
includes taxes & fees
18 May - 19 May
Luxury 3 BR Near NYC with Easy Parking

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is £411
includes taxes & fees
29 May - 30 May
Luxury 3BR Home Game Room Free Parking

3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (1 review)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveller
The price is £539
includes taxes & fees
18 May - 19 May
3BR Prime Luxury near NYC w Arcade Room

Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is £909
includes taxes & fees
18 May - 19 May
Two Wash

NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.0 out of 10, (4 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is £203
includes taxes & fees
20 May - 21 May
NY Luxury Apt Free Parking in PRIME Area

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is £444
includes taxes & fees
18 May - 19 May
Spacious 3BR Luxe Escape near NYC

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is £906
includes taxes & fees
18 May - 19 May
Prime Luxe 3-BR NYC - Free Parking

3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is £948
includes taxes & fees
18 May - 19 May
3BR Prime Luxury NY - Free Parking

Global Luxury Suites at The Arches

Global Luxury Suites at The Arches
2.5 star property
Bronx
6.8 out of 10, (589 reviews)
"Very nice stay "
United States
Massaran
The price is £162
includes taxes & fees
25 May - 26 May
Global Luxury Suites at The Arches

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is £256
includes taxes & fees
19 May - 20 May
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
8.0 out of 10, Very good, (1 review)
"The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays."
United States
Adj Fatou
The price is £412
includes taxes & fees
18 May - 19 May
Uscale 2BR Escape in the Heart of NYC

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
6.8 out of 10, (3 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is £405
includes taxes & fees
18 May - 19 May
Luxury 3BR Family Home Game Room Parking

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
4.8 out of 10, (6 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is £238
includes taxes & fees
19 May - 20 May
Luxury 1BR located in Prime Yonkers Area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is £584
includes taxes & fees
18 May - 19 May
Luxury NYC Home Game Room Free Parking

Global Luxury Suites White Plains

Global Luxury Suites White Plains
3.5 star property
White Plains
6.8 out of 10, (43 reviews)
"Please stay away from this horrible place!!! I have travelled all over the world but never dealt with such terrible company and their property. "
United States
Katerine
The price is £275
includes taxes & fees
18 May - 19 May
Global Luxury Suites White Plains
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, apart-hotels, 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 £124 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 Planting Fields Arboretum State Historic Park and Theodore Roosevelt Memorial 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.