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

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Our top choices for Oyster Bay vacation 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, (84 reviews)
"A beautiful home and you cannot beat the views and location!"
United States
Daniel M.
The price is CA $287
CA $658 total
includes taxes & fees
Sep 21 - Sep 22
Captain's Cottage - Cold Spring Harbor Water Views

2. 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 CA $309
CA $583 total
includes taxes & fees
Sep 14 - Sep 15
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

3. 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 CA $125
CA $217 total
includes taxes & fees
Sep 15 - Sep 16
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

4. 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 CA $347
CA $631 total
includes taxes & fees
Sep 20 - Sep 21
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

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 CA $326
CA $597 total
includes taxes & fees
Oct 12 - Oct 13
Luxe Provincial Style Studio w/ Patio & Parking

6. 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, (21 reviews)
"Everything was good"
United States
Elena
The price is CA $165
CA $275 total
includes taxes & fees
Sep 15 - Sep 16
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

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 CA $122
CA $227 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Studio by Hofstra University

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

The Stone House! Pvt Entry/Sleeps 4 - by Hofstra
Uniondale
10.0 out of 10, Exceptional, (14 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 CA $191
CA $302 total
includes taxes & fees
Sep 22 - Sep 23
The Stone House! Pvt Entry/Sleeps 4 - by Hofstra

9. 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 CA $160
CA $378 total
includes taxes & fees
Sep 14 - Sep 15
Cozy Home.

10. 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 CA $305
CA $576 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

11. 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 CA $267
CA $525 total
includes taxes & fees
Sep 15 - Sep 16
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

12. 2 Pvt bed Rm 1bathroom no kitchen attic

2 Pvt bed Rm 1bathroom no kitchen attic
Uniondale
9.0 out of 10, Wonderful, (8 reviews)
"The overall stay was very warm & welcoming. Suitable for kids! "
United States
Tea-Anna S.
The price is CA $164
CA $277 total
includes taxes & fees
Sep 15 - Sep 16
2 Pvt bed Rm 1bathroom no kitchen attic

13. 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 CA $215
CA $418 total
includes taxes & fees
Sep 14 - Sep 15
Julie's Cozy 2 Bedroom Basement Apartment

14. 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
8.0 out of 10, Very good, (5 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 CA $235
CA $313 total
includes taxes & fees
Sep 25 - Sep 26
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

15. 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 CA $586
CA $996 total
includes taxes & fees
Sep 22 - Sep 23
Huntington Village House 4BR – Walk to everything

16. Tremendous 1-bedroom apartment with AC in Hempstead

Tremendous 1-bedroom apartment with AC in Hempstead
Hempstead
The price is CA $118
CA $163 total
includes taxes & fees
Sep 26 - Sep 27
Tremendous 1-bedroom apartment with AC in Hempstead

17. 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 CA $137
CA $228 total
includes taxes & fees
Sep 14 - Sep 15
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

18. Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (15 reviews)
"Love being able to park off the street."
United States
Joan
The price is CA $147
CA $297 total
includes taxes & fees
Sep 21 - Sep 22
Your Perfect Getaway Between Farmingdale & Amityville

19. 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 CA $599
CA $873 total
includes taxes & fees
Oct 1 - Oct 2
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

20. Majestically Pleasant Suite

Majestically Pleasant Suite
Hempstead
8.0 out of 10, Very good, (3 reviews)
"I really liked how quiet and clean the place was. Would 100% stay here again!!"
United States
Ashley
The price is CA $276
CA $347 total
includes taxes & fees
Sep 14 - Sep 15
Majestically Pleasant Suite
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oyster Bay. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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?

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

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 Center Island 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.