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

Oyster Bay Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Oyster Bay vacation rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (190 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$151 nightly
The price is $174
Oct 12 - Oct 13
Total with taxes and fees
Stamford Suites
Interior

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

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
$427 nightly
The price is $488
Oct 22 - Oct 23
Total with taxes and fees
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

3. 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
$294 nightly
The price is $339
Oct 12 - Oct 13
Total with taxes and fees
Guesthouse at Norwalk Inn
A flat-screen TV mounted on a black entertainment center in a room with a dining area visible through the glass door.

4. Home & Away Hotel-Style

Home & Away Hotel-Style
2.0 star property
Bronx
$300 nightly
The price is $348
Oct 27 - Oct 28
Total with taxes and fees
Home & Away Hotel-Style
A white shelving unit with decorative items, including a mixtape box, two golden bird figurines, and three glass vases.

5. 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
$262 nightly
The price is $300
Oct 15 - Oct 16
Total with taxes and fees
Sundown Escape-South Shore Long Island
A wooden deck with a white railing, a stone pathway, and a white fence in the background.

6. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
$278 nightly
The price is $318
Oct 19 - Oct 20
Total with taxes and fees
Spacious 3BR Family Home Near Everything
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

7. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
$329 nightly
The price is $377
Oct 12 - Oct 13
Total with taxes and fees
Elegant Hideaway with Free Parking
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

8. Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (2 reviews)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
$611 nightly
The price is $680
Oct 12 - Oct 13
Total with taxes and fees
Luxury NYC Home with Free Parking for 12
A living room with a sectional sofa, a white armchair, a patterned rug, and a wooden floor.

9. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
7.0 out of 10, Good, (4 reviews)
"My family and I were satisfy with the stay I’ll definitely coming back"
United States
Josephine
Spacious 3BR Luxe Escape near NYC
A modern interior with a glass wall, seating area, and a view of the city.

10. The Arches Suites

The Arches Suites
3.5 star property
Bronx
$188 nightly
The price is $219
Nov 3 - Nov 4
Total with taxes and fees
The Arches Suites
A modern living room with a stone wall, a flat-screen TV, a white sofa, and a kitchen area with a bar counter and chairs.

11. Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
2.0 out of 10, (2 reviews)
"My experience did not match the listing. I was asked to make payment outside the platform and the check-in process was not clear. I would not recommend this property. ⸻ ⭐⭐ Balanced Review The property did not meet expectations. When I arrived, the check-in process was unclear and the home appeared to be partially occupied. I was also instructed to make a payment outside of Hotels.com instead of using the platform. This caused confusion and concern. I would suggest the listing be...
United States
Dianelly
$482 nightly
The price is $539
Oct 12 - Oct 13
Total with taxes and fees
Luxe 1BR Oasis - Prime NY Stay
A two-story house with a front porch, a garage, and a well-maintained lawn.

12. Great Neck Basecamp: Steps to Downtown & Rail

Great Neck Basecamp: Steps to Downtown & Rail
3.0 star property
Great Neck
$378 nightly
The price is $422
Oct 12 - Oct 13
Total with taxes and fees
Great Neck Basecamp: Steps to Downtown & Rail
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

13. Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
9.0 out of 10, Wonderful, (2 reviews)
"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
$491 nightly
The price is $549
Oct 12 - Oct 13
Total with taxes and fees
Uscale 2BR Escape in the Heart of NYC
A modern living room with a beige sectional sofa, a green armchair, a marble-patterned rug, a gold coffee table, and a flat-screen TV mounted on a white wall.

14. Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
4.4 out of 10, (6 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
$482 nightly
The price is $539
Oct 12 - Oct 13
Total with taxes and fees
Luxury 3BR Family Home Game Room Parking
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

15. Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
$535 nightly
The price is $599
Oct 12 - Oct 13
Total with taxes and fees
Luxury 3 BR Near NYC with Easy Parking
A modern living room with a sofa, armchairs, and a glass coffee table.

16. Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking
2.0 star property
Bryn Mawr
2.0 out of 10, (1 review)
$783 nightly
The price is $876
Oct 12 - Oct 13
Total with taxes and fees
Luxury 5 BR Home Free Parking
A modern living room with a white sofa, a glass coffee table, and a round armchair. There is a wooden floor and a large window with curtains.

17. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
2.0 out of 10, (3 reviews)
"Very inaccurate listing upon arriving host called me stating I could not stay at property due to issues on their end instead of offering a refund I was sent to a different property that was a 1 bedroom with 1 bed that was clearly not cleaned instead of the 3 bedroom 5 bed luxury house I initially booked I explained this would not work for me and my 4 other guests and got told there was no other choice and hung up on, me and my guests had no option beside to go back home very bad experience DO...
United States
Gerald
$583 nightly
The price is $652
Oct 12 - Oct 13
Total with taxes and fees
Spacious 3BR Luxe Escape near NYC
A modern kitchen with white cabinets, a central island with stools, a stone accent wall, a flat-screen TV, and a beige sofa with teal cushions.

18. 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
$492 nightly
The price is $551
Oct 12 - Oct 13
Total with taxes and fees
Luxury 1BR located in Prime Yonkers Area
A modern bedroom with a large bed, white bedding, a nightstand, a wall-mounted lamp, and a window with sheer curtains.

19. 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
$680 nightly
The price is $778
Oct 13 - Oct 14
Total with taxes and fees
Luxury NYC Home Game Room Free Parking
A modern kitchen with white cabinetry, a dining area with a glass table, and a view of the outdoors through large windows.

20. Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC
4.0 star property
Southeast Yonkers
3.6 out of 10, (4 reviews)
"We never got to stay because THERE WAS ANOTHER FAMILY THERE. THAT WOMEN SAID SHE WAS RENTING THE HOUSE FOR ANOTHER MONTH. "
United States
Angel
$583 nightly
The price is $652
Oct 14 - Oct 15
Total with taxes and fees
Modern Comfort in the Heart of NYC
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oyster Bay Hotel Reviews

Comfort Inn JFK Airport

Comfort Inn JFK Airport

8/10 Good
"thanks"
Vivian 1-night trip
Posted less than an hour ago
Comfort Inn JFK Airport

Find out more about Oyster Bay

Everything you need to know about Oyster Bay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oyster Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oyster Bay vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oyster Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $117 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oyster Bay rentals

At Expedia, we put the best Oyster Bay vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Oyster Bay?

Yes, there are vacation rentals in Oyster Bay near Planting Fields Arboretum State Historic Park, or you can select a more remote option if you want a relaxing stay. Oyster Bay is known for its shopping and restaurants.

What are some of the best vacation rentals in Oyster Bay?

Modern Luxury Home w GameRoom & Parking: You might like this vacation home rental near Oyster Bay. It is situated near the airport and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Oyster Bay?

Expedia has 3 vacation 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 Beekman Beach are other places to visit while you're in town.

What’s a vacation rental in Oyster Bay like?

A vacation rental is a private property you can book for a few weeks or just a few days in Oyster Bay. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family getaway.