Photo by Wanderlust Nomad

Holiday Homes in Oyster Bay

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec
In four months
16 Jan - 18 Jan

Featured Holiday Homes in Oyster Bay and around

Charming 1-bedroom house with WiFi, AC in delightful Uniondale
Interior

Charming 1-bedroom house with WiFi, AC in delightful Uniondale

9.6 out of 10, Exceptional, (22)
"Outstanding accommodation, the host was extremely helpful and the place very clean and quiet most of all. "
The price is €146
includes taxes & fees
15 Oct - 16 Oct
Charming 1-bedroom house with WiFi, AC in delightful Uniondale
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Fridge, microwave, oven, stovetop

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

8.8 out of 10, Excellent, (40)
"Very clean, comfortable, and quiet property. Although advertised one car parking, actually can park 2, which is good since limited street parking in a crowded neighborhood. Highly recommended if you're staying in the NYC area."
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Property grounds

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.4 out of 10, Exceptional, (12)
"Perfect place to rest. Excellent service! "
The price is €173
includes taxes & fees
24 Sept - 25 Sept
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
NEWLY RENOVATED MODERN 4BR, 3BTH COLONIAL HOME 2 LEVELS AC Near All, NYC Access
Fridge, microwave, oven, stovetop

NEWLY RENOVATED MODERN 4BR, 3BTH COLONIAL HOME 2 LEVELS AC Near All, NYC Access

10.0 out of 10, Exceptional, (1)
"The property was very cozy and well put together "
NEWLY RENOVATED MODERN 4BR, 3BTH COLONIAL HOME 2 LEVELS AC Near All, NYC Access
Charming 3-bedroom modern family retreat!
Property grounds

Charming 3-bedroom modern family retreat!

9.0 out of 10, Wonderful, (4)
"Spacious, clean and host was very responsive to any questions we had ! "
The price is €469
includes taxes & fees
1 Oct - 2 Oct
Charming 3-bedroom modern family retreat!
Elegant 5BR Family Oasis – 5 Mins to JFK, Walk to Mall & Train, Free Parking!
Fridge, microwave, oven, stovetop

Elegant 5BR Family Oasis – 5 Mins to JFK, Walk to Mall & Train, Free Parking!

10.0 out of 10, Exceptional, (1)
"Great location and helpful owner! Just minutes from JFK, short drive to Flushing Meadows and LaGuardia. Had a good time with extended family. Comfy beds, furniture. Some small hiccups in a newly refurbed place and first-time rental, for example, soap, salt-pepper, and 3 fun functional restrooms items should help. Owner went out of their way to hurry construction/repair, helped with early checkin and had great communication throughout. Easily slept 9 with room to spare, and couches seated the...
Elegant 5BR Family Oasis – 5 Mins to JFK, Walk to Mall & Train, Free Parking!
3BR Prime Luxury near NYC w Arcade Room
Terrace/patio

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
8.0 out of 10, Very good, (1)
"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."
The price is €652
includes taxes & fees
24 Sept - 25 Sept
3BR Prime Luxury near NYC w Arcade Room
Sophisticated Suite Near JFK Airport
Interior

Sophisticated Suite Near JFK Airport

2.0 star property
9.6 out of 10, Exceptional, (4)
"I liked the property never nice the host was cool too. Definitely would stay again "
The price is €221
includes taxes & fees
28 Sept - 29 Sept
Sophisticated Suite Near JFK Airport
Beautiful historic home in Stony Brook!
Interior

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very good, (14)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Exterior

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

2.0 star property
9.6 out of 10, Exceptional, (5)
"We had such a nice and peaceful stay! Shelton’s place was super clean, quiet, comfortable, and had everything we needed. Would definitely stay here again! "
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Walkable to all in Downtown Seaford! Clean 1 bed basement unit
Property grounds

Walkable to all in Downtown Seaford! Clean 1 bed basement unit

9.6 out of 10, Exceptional, (10)
"We were so happy to find this little gem in Seaford! Perfect location and perfect little home away from home. It has everything you need and easy access to everything nearby. We look forward to staying there again when we visit LI!"
Walkable to all in Downtown Seaford! Clean 1 bed basement unit
Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Property grounds

Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10.0 out of 10, Exceptional, (4)
"Lovely little home in Stamford."
The price is €310
includes taxes & fees
24 Sept - 25 Sept
Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Spacious 4-bedroom house in charming Rye with AC
Miscellaneous

Spacious 4-bedroom house in charming Rye with AC

The price is €396
includes taxes & fees
24 Sept - 25 Sept
Spacious 4-bedroom house in charming Rye with AC
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

9.4 out of 10, Exceptional, (29)
"its small but very nice for a short stay would recommend."
The price is €143
includes taxes & fees
29 Sept - 30 Sept
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Luxury 5BR 2BA Spacious Home NYC Free Parking + Office
Living area

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

2.0 out of 10, (1)
"If I could give this place zero stars, I would. Upon arrival, I received no check-in information, which immediately set the tone for a frustrating experience. When I got to the property, the front door was already open, raising serious concerns about security. Inside, the floors were dirty, the beds were unmade, and the trash from the previous guests had not been removed. There were bugs throughout the space, and the front door handle was broken, making the property feel unsafe and poorly...
Luxury 5BR 2BA Spacious Home NYC Free Parking + Office
Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow
Property grounds

Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow

9.0 out of 10, Wonderful, (10)
"Perfect location to enjoy Northport! Everything is within walking distance. Host was very helpful and accommodating. Great stay and will definitely return! "
The price is €974
includes taxes & fees
29 Sept - 30 Sept
Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow
Majestically Pleasant Suite
TV

Majestically Pleasant Suite

The price is €219
includes taxes & fees
28 Sept - 29 Sept
Majestically Pleasant Suite
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Marina

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (66)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time
Property grounds

BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

10.0 out of 10, Exceptional, (10)
"Super enjoyable."
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time
Modern 4BD/3BA w/Parking & deck & 29 min>NYC
Outdoor dining

Modern 4BD/3BA w/Parking & deck & 29 min>NYC

9.6 out of 10, Exceptional, (19)
"The house was very clean and the check-in process was smooth. Host was very responsive. Overall we loved our stay and would definitely book again next time we're in the area!"
Modern 4BD/3BA w/Parking & deck & 29 min>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

Holiday Inn Express Jamaica - JFK AirTrain - NYC by IHG

Holiday Inn Express Jamaica - JFK AirTrain - NYC by IHG

10/10 Excellent
"It’s an excellent property in a great location!"
Paul 1-night trip
Posted 21 hours ago
Holiday Inn Express Jamaica - JFK AirTrain - NYC by IHG

Find out more about Oyster Bay

Find out more about Oyster Bay

Oyster Bay Holiday Homes information

Number of reviews
236
Accommodation
673 Holiday Homes
Lowest Price
€143
Highest Price
€974

Explore a world of travel with Expedia

Explore a world of travel with Expedia