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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Oyster Bay holiday 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, (198 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is RM690
RM793 total
includes taxes & fees
2 Nov - 3 Nov
Stamford Suites
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

2. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is RM1,467
RM1,687 total
includes taxes & fees
26 Oct - 27 Oct
Guesthouse at Norwalk Inn
Interior

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

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
The price is RM494
RM1,992 total
includes taxes & fees
28 Oct - 29 Oct
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
A modern gym with treadmills, weight machines, and free weights.

4. The Arches Suites

The Arches Suites
2.0 star property
Bronx
The price is RM533
RM1,034 total
includes taxes & fees
17 Nov - 18 Nov
The Arches Suites
A bedroom with a bed, bedside tables, a mirror, a bench, and a wall sign.

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
The price is RM541
RM1,224 total
includes taxes & fees
26 Oct - 27 Oct
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
The price is RM705
RM1,210 total
includes taxes & fees
26 Oct - 27 Oct
Spacious 3BR Family Home Near Everything
A breakfast buffet with pastries, fruits, and a coffee station.

7. 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, (3 reviews)
"It was a fraude. You pay but property Is not to rent. I lost my money."
United States
daniel
The price is RM1,655
RM2,574 total
includes taxes & fees
26 Oct - 27 Oct
Luxury NYC Home with Free Parking for 12
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

8. 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
The price is RM1,283
RM2,085 total
includes taxes & fees
26 Oct - 27 Oct
Uscale 2BR Escape in the Heart of NYC
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
The price is RM1,655
RM2,460 total
includes taxes & fees
26 Oct - 27 Oct
Spacious 3BR Luxe Escape near NYC
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

10. 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
The price is RM2,022
RM2,922 total
includes taxes & fees
26 Oct - 27 Oct
Luxury NYC Home Game Room Free Parking
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
The price is RM1,103
RM1,843 total
includes taxes & fees
23 Nov - 24 Nov
Luxe 1BR Oasis - Prime NY Stay
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

12. Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
2.0 out of 10, (1 review)
"This is a scam and at the same time others guest’s was there for same booking but we can’t get any feed the property support and we returned from the property and kids suffered a lot!!!"
United States
Md Asadul
The price is RM1,479
RM2,263 total
includes taxes & fees
26 Oct - 27 Oct
Luxury 3 BR Near NYC with Easy Parking
A two-story house with a front porch, a garage, and a well-maintained lawn.

13. Great Neck Basecamp: Steps to Downtown & Rail

Great Neck Basecamp: Steps to Downtown & Rail
3.0 star property
Great Neck
The price is RM756
RM1,820 total
includes taxes & fees
26 Oct - 27 Oct
Great Neck Basecamp: Steps to Downtown & Rail
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
3.8 out of 10, (8 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is RM1,155
RM1,901 total
includes taxes & fees
26 Oct - 27 Oct
Luxury 3BR Family Home Game Room Parking
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

15. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
The price is RM732
RM1,446 total
includes taxes & fees
26 Oct - 27 Oct
Elegant Hideaway with Free Parking
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.

16. 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
The price is RM1,103
RM1,843 total
includes taxes & fees
24 Nov - 25 Nov
Luxury 1BR located in Prime Yonkers Area
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
The price is RM1,655
RM2,460 total
includes taxes & fees
26 Oct - 27 Oct
Spacious 3BR Luxe Escape near NYC
A modern kitchen with white cabinetry, a dining area with a glass table, and a view of the outdoors through large windows.

18. Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC
4.0 star property
Southeast Yonkers
3.2 out of 10, (5 reviews)
"LIARS! these people take your money, when you go check in you'll find they aren't the real hosts. and house is already rented long term. NOT A TRUE LISTING!"
United States
Carlos Enrique
The price is RM1,655
RM2,460 total
includes taxes & fees
26 Oct - 27 Oct
Modern Comfort in the Heart of NYC
A modern kitchen with white cabinets, a granite countertop, a built-in oven, a stove, and a variety of appliances including a coffee maker and a blender.

19. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is RM3,493
RM4,499 total
includes taxes & fees
26 Oct - 27 Oct
Prime Luxe 3-BR NYC - Free Parking
A breakfast buffet with pastries, fruits, and a coffee station.

20. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is RM3,677
RM4,704 total
includes taxes & fees
26 Oct - 27 Oct
3BR Prime Luxury NY - Free Parking
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
"Excelente limpieza, buen desayuno, lo recomiendo."
Jose 2-night trip
Posted 9 hours ago
Highbridge Hotel

Find out more about Oyster Bay

Search for holiday rentals in Oyster Bay on Expedia.co.uk! 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
  • Use the map to find apartments and other holiday homes in the Oyster Bay neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oyster Bay while they last

Look no further and take a look at our great range of rental properties in Oyster Bay!

Frequently asked questions

Can I find a holiday rental in Oyster Bay?

Yes, there are holiday rentals in Oyster Bay close to Planting Fields Arboretum State Historic Park, or you can select a more secluded option if you're looking for a relaxing stay. Oyster Bay is known for its shopping and restaurants.

What are some of the best holiday rentals that Oyster Bay has to offer?

Modern Luxury Home w GameRoom & Parking: This holiday home rental outside Oyster Bay 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 that you can cook with friends or family.

How many holiday rentals are there in Oyster Bay?

Expedia has 3 holiday 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 holiday rental in Oyster Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oyster Bay. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for family trips or small group gatherings.