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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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Oyster Bay vacation rentals

A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

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, (86 reviews)
"A beautiful home and you cannot beat the views and location!"
United States
Daniel M.
$480 nightly
The price is $548
Oct 5 - Oct 6
Total with taxes and fees
Captain's Cottage - Cold Spring Harbor Water Views
A modern kitchen with dark cabinetry, a microwave, and a stove. There is a large flat-screen TV mounted on the wall.

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.
$369 nightly
The price is $422
Oct 19 - Oct 20
Total with taxes and fees
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
A modern kitchen with a marble island, bar stools, and a built-in oven.

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.
$400 nightly
The price is $457
Oct 6 - Oct 7
Total with taxes and fees
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
A modern bedroom with a large bed, a small dining area, and a kitchenette.

4. 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
$383 nightly
The price is $438
Oct 2 - Oct 3
Total with taxes and fees
Luxe Provincial Style Studio w/ Patio & Parking
A modern kitchen with wooden cabinets and a granite countertop.

5. Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (16 reviews)
"Love being able to park off the street."
United States
Joan
$190 nightly
The price is $217
Oct 5 - Oct 6
Total with taxes and fees
Your Perfect Getaway Between Farmingdale & Amityville
A living room with a sofa, a coffee table, a wicker chair, a ceiling fan, and a large window with a view of a parked car outside.

6. 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.
$651 nightly
The price is $744
Oct 27 - Oct 28
Total with taxes and fees
Huntington Village House 4BR – Walk to everything
A hotel room with a bed, desk, chair, and a TV.

7. 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.
$145 nightly
The price is $162
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

8. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (186 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$159 nightly
The price is $183
Oct 12 - Oct 13
Total with taxes and fees
Stamford Suites
A two-story house with a front porch, a red hexagonal tile pathway leading to the door, and a well-maintained lawn.

9. 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, (23 reviews)
"Everything was good"
United States
Elena
$185 nightly
The price is $207
Oct 4 - Oct 5
Total with taxes and fees
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!
A modern kitchen with granite countertops, stainless steel appliances, and white cabinetry.

10. 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
$573 nightly
The price is $655
Oct 12 - Oct 13
Total with taxes and fees
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
A beach with a sandy shore, a few fishing rods, and a tent.

11. 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
$192 nightly
The price is $214
Oct 4 - Oct 5
Total with taxes and fees
The Stone House! Pvt Entry/Sleeps 4 - by Hofstra
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

12. 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.
$293 nightly
The price is $331
Oct 6 - Oct 7
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A bedroom with a bed, a nightstand, a mirror, and a window with curtains.

13. 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, (53 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
$144 nightly
The price is $165
Oct 3 - Oct 4
Total with taxes and fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

14. Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
$368 nightly
The price is $417
Oct 2 - Oct 3
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford
Exterior

15. Welcoming 1 bedroom apartment in beautiful harbor village.

Welcoming 1 bedroom apartment in beautiful harbor village.
Northport
10.0 out of 10, Exceptional, (1 review)
"Beautiful clean upstairs apartment with a private entrance. Very quiet neighborhood with a small park across the street. Karen, the homeowner who lives downstairs is a wonderful person. The place was perfect for what I needed amd the location was great."
United States
Sallyann S.
$275 nightly
The price is $314
Oct 5 - Oct 6
Total with taxes and fees
Welcoming 1 bedroom apartment in beautiful harbor village.
A covered porch with a tiled floor, a hanging light fixture, and a view of a street with parked cars and houses.

16. 2 Pvt bed Rm 1bathroom no kitchen attic

2 Pvt bed Rm 1bathroom no kitchen attic
Uniondale
9.2 out of 10, Wonderful, (10 reviews)
"Parking on the street was always available."
United States
William
$174 nightly
The price is $195
Oct 5 - Oct 6
Total with taxes and fees
2 Pvt bed Rm 1bathroom no kitchen attic
A modern bedroom with a large bed, a bedside table, a sofa, and a potted plant.

17. 1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.6 out of 10, Excellent, (25 reviews)
"Exactly as advertised, comfortable bed easy entry, overall great experience."
United States
Monte P.
$154 nightly
The price is $176
Oct 4 - Oct 5
Total with taxes and fees
1 bedroom 1 bath private entrance
A bedroom with a bed, bedside tables, a nightstand, a desk, and a chair.

18. 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.
$174 nightly
The price is $180
Oct 6 - Oct 7
Total with taxes and fees
Cozy Studio by Hofstra University
A modern living room with a sofa, a coffee table, and a bar stool.

19. 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.
$278 nightly
The price is $315
Oct 4 - Oct 5
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A living room with a sofa, a glass coffee table, a fireplace, and a TV mounted above it.

20. 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.
$364 nightly
The price is $416
Oct 4 - Oct 5
Total with taxes and fees
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
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

Comfort Inn JFK Airport

Comfort Inn JFK Airport

8/10 Good
"Unfortunately, there are staffing issues. This limited the services such as the bar area."
Dana 1-night trip
Posted 1 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 $176 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.