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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Oyster Bay vacation rentals

Marina

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, (81 reviews)
"Perfect spot. Gorgeous view. "
United States
Trina A.
The price is ￥56,840
￥108,170 total
includes taxes & fees
Jul 26 - Jul 27
Captain's Cottage - Cold Spring Harbor Water Views
Interior

Family-Friendly Retreat w/ Trampoline & Grill

Family-Friendly Retreat w/ Trampoline & Grill
Locust Valley
6.0 out of 10, (1 review)
The price is ￥24,360
￥67,438 total
includes taxes & fees
Jul 20 - Jul 21
Family-Friendly Retreat w/ Trampoline & Grill
1 bedroom, WiFi

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (4 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 ￥31,668
￥62,530 total
includes taxes & fees
Jul 20 - Jul 21
Luxe Provincial Style Studio w/ Patio & Parking
Coffee/tea maker, spices

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 ￥33,292
￥64,383 total
includes taxes & fees
Aug 10 - Aug 11
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
1 bedroom, in-room safe, desk, WiFi (free)

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)
"Had a great stay "
United States
Desiree
The price is ￥16,727
￥27,736 total
includes taxes & fees
Aug 10 - Aug 11
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
1 bedroom, iron/ironing board, WiFi (free), bed sheets

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, (8 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is ￥30,856
￥61,602 total
includes taxes & fees
Jul 27 - Jul 28
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
1 bedroom, iron/ironing board, WiFi (free), bed sheets

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is ￥15,347
￥21,898 total
includes taxes & fees
Jul 21 - Jul 22
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Dining

Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.

Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.
Hicksville
9.6 out of 10, Exceptional, (4 reviews)
"We were in town with our family celebrating my son’s wedding. The house was very clean and spacious. Our host was very responsive and helpful during our stay. We will definitely be back whenever we come back to visit!"
United States
Darryl S.
The price is ￥127,776
￥241,065 total
includes taxes & fees
Jul 20 - Jul 21
Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.
Coffee/tea maker, fridge, microwave, oven

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, (11 reviews)
"Perfect stay ! Owners were beyond helpful and responsive. Their kindness helpedOur family during a difficult transition between buying and selling a home. "
United States
Christina C.
The price is ￥69,670
￥102,608 total
includes taxes & fees
Aug 9 - Aug 10
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (138 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is ￥24,198
￥27,828 total
includes taxes & fees
Aug 2 - Aug 3
Stamford Suites
Property grounds

2 Pvt bed Rm 1bathroom no kitchen attic

2 Pvt bed Rm 1bathroom no kitchen attic
Uniondale
8.8 out of 10, Excellent, (6 reviews)
"The overall stay was very warm & welcoming. Suitable for kids! "
United States
Tea-Anna S.
The price is ￥18,579
￥31,616 total
includes taxes & fees
Jul 20 - Jul 21
2 Pvt bed Rm 1bathroom no kitchen attic
1 bedroom, iron/ironing board, WiFi (free), bed sheets

Cozy Freeport Retreat / 8 min Loffs Lake / Pets 🐶

Cozy Freeport Retreat / 8 min Loffs Lake / Pets 🐶
Freeport
7.6 out of 10, Good, (15 reviews)
"Great stay "
United States
Lindsay
The price is ￥16,808
￥39,609 total
includes taxes & fees
Jul 20 - Jul 21
Cozy Freeport Retreat / 8 min Loffs Lake / Pets 🐶
1 bedroom, iron/ironing board, WiFi (free), bed sheets

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, (46 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 ￥18,270
￥29,226 total
includes taxes & fees
Jul 20 - Jul 21
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Property grounds

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
7.6 out of 10, Good, (4 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 ￥25,578
￥33,971 total
includes taxes & fees
Jul 22 - Jul 23
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
TV

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 ￥35,728
￥67,053 total
includes taxes & fees
Jul 21 - Jul 22
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Outdoor spa tub

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, (12 reviews)
"Wonderful stay"
United States
Kenneth B.
The price is ￥487,005
￥673,851 total
includes taxes & fees
Aug 1 - Aug 2
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Luxury Apartment | Living area

NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.8 out of 10, (7 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is ￥17,685
￥43,984 total
includes taxes & fees
Aug 7 - Aug 8
NY Luxury Apt Free Parking in PRIME Area
1 bedroom, iron/ironing board, WiFi (free), bed sheets

Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (7 reviews)
"It was relaxing very comfortable "
United States
Julian R.
The price is ￥17,978
￥36,311 total
includes taxes & fees
Aug 2 - Aug 3
Your Perfect Getaway Between Farmingdale & Amityville
Beach

It's a Loft on the Second floor. Mins away from UBS Arena, JFK Airport

It's a Loft on the Second floor. Mins away from UBS Arena, JFK Airport
Elmont
9.4 out of 10, Exceptional, (53 reviews)
"Nice location, clean apartment."
United States
Neil
The price is ￥18,514
￥44,415 total
includes taxes & fees
Jul 20 - Jul 21
It's a Loft on the Second floor. Mins away from UBS Arena, JFK Airport
Exterior detail

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, (17 reviews)
"Cute little apt . Perfect location highly recommend"
United States
Kristin
The price is ￥16,240
￥28,824 total
includes taxes & fees
Jul 30 - Jul 31
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!
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

Highbridge Hotel

Highbridge Hotel

10/10 Excellent
"Clean and comfortable room"
Jill 1-night trip
Posted less than an hour ago
Highbridge Hotel

Find out more about Oyster Bay

Search for holiday rentals in Oyster Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Oyster Bay using one of the methods below:

  • View our selection of featured holiday rentals in Oyster Bay
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Look no further and take a look at our great range of rental properties in Oyster Bay!

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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental near Oyster Bay is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 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 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.