Oakdale Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oakdale holiday rentals

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is HK$1,686
HK$2,702 total
includes taxes & fees
6 May - 7 May
Spacious 3BR Family Home Near Everything

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (25 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
The price is HK$2,100
HK$4,243 total
includes taxes & fees
4 May - 5 May
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
10.0 out of 10, Exceptional, (4 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is HK$2,962
HK$5,398 total
includes taxes & fees
4 May - 5 May
Modern Vacation home. Close to The Hamptons

Peaceful private 2-bedroom house in Bayport. Amazing location!

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
10.0 out of 10, Exceptional, (2 reviews)
"Quiet and respectful owner. Welcoming and a great nights sleep. "
United States
Jason P.
The price is HK$1,904
HK$2,488 total
includes taxes & fees
7 May - 8 May
Peaceful private 2-bedroom house in Bayport. Amazing location!

THE OASIS @ LONG ISLAND

THE OASIS @ LONG ISLAND
Huntington Station
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
The price is HK$1,959
HK$3,813 total
includes taxes & fees
4 May - 5 May
THE OASIS @ LONG ISLAND

Charming Rocky Point Home ~ 1 Mi to Beach!

Charming Rocky Point Home ~ 1 Mi to Beach!
3.0 star property
Rocky Point
The price is HK$2,570
HK$4,825 total
includes taxes & fees
24 May - 25 May
Charming Rocky Point Home ~ 1 Mi to Beach!

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (29 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is HK$4,838
HK$10,406 total
includes taxes & fees
6 May - 7 May
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
The price is HK$1,152
HK$2,032 total
includes taxes & fees
4 May - 5 May
Sundown Escape-South Shore Long Island

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026
Center Moriches
10.0 out of 10, Exceptional, (116 reviews)
"Quick and kind communication, beautiful location and the most comfortable beds! An absolute must-stay for anyone coming to the area."
United States
Stephanie M.
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (22 reviews)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is HK$1,818
HK$5,433 total
includes taxes & fees
6 May - 7 May
3 Story Beach Waterview, 3 KING bed, golf putting green!

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, (40 reviews)
"I found everything to be clean and fresh. Owners were nice. I would stay there again. "
United States
Mark
The price is HK$832
HK$1,354 total
includes taxes & fees
4 May - 5 May
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

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, (76 reviews)
"Location was perfect!"
United States
Linda J P.
The price is HK$2,115
HK$4,404 total
includes taxes & fees
11 May - 12 May
Captain's Cottage - Cold Spring Harbor Water Views

Tranquil Stay

Tranquil Stay
Shirley
8.0 out of 10, Very good, (10 reviews)
"The property was spacious, clean and well kept. We only stayed one night but enjoyed our time. We definitely would stay again. "
United States
Ellen C.
The price is HK$2,322
HK$4,390 total
includes taxes & fees
10 May - 11 May
Tranquil Stay

Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC
Northport
9.4 out of 10, Exceptional, (16 reviews)
"Our host, Richard, was exceptional. The home was charming, great location and perfect for us!"
United States
Laura H.
Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 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 HK$1,528
HK$3,017 total
includes taxes & fees
4 May - 5 May
Luxe Provincial Style Studio w/ Patio & Parking

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 HK$1,152
HK$4,300 total
includes taxes & fees
29 May - 30 May
Shop, Hike, Golf & Swim: Inviting Deer Park Escape

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, (9 reviews)
"Wonderful stay"
United States
Kenneth B.
The price is HK$3,711
HK$5,868 total
includes taxes & fees
5 May - 6 May
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

Bright airy Fair Harbor home with ocean views steps from the soft sandy beach

Bright airy Fair Harbor home with ocean views steps from the soft sandy beach
Fire Island
9.6 out of 10, Exceptional, (4 reviews)
"Perfect Fire Island getaway. Great location and beautiful beach home. Would recommend and love to come back!"
United States
Jessica W.
The price is HK$6,660
HK$10,222 total
includes taxes & fees
4 May - 5 May
Bright airy Fair Harbor home with ocean views steps from the soft sandy beach

South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (4 reviews)
"Really nice and great price! Would stay again. "
United States
Philip P.
The price is HK$1,058
HK$1,781 total
includes taxes & fees
5 May - 6 May
South Shore Studio in Mastic

Luxurious Waterfront all Season Home with Private Beach. Awesome sunsets!

Luxurious Waterfront all Season Home with Private Beach. Awesome sunsets!
Shirley
9.8 out of 10, Exceptional, (39 reviews)
"Very peaceful, the house had everything we needed and we comfortable and clean, but what was special was the outside deck and water… we all just sat outside on the deck just enjoying the peace and serenity of the location "
United States
tamara h.
The price is HK$4,662
HK$8,897 total
includes taxes & fees
25 May - 26 May
Luxurious Waterfront all Season Home with Private Beach. Awesome sunsets!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Oakdale Hotel Reviews

Find out more about Oakdale

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

  • View our selection of featured holiday rentals in Oakdale
  • Use the map to find apartments and other holiday homes in the Oakdale neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakdale while they last

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

Frequently asked questions

Are there holiday rentals in Oakdale?

Yes, there are holiday rentals in Oakdale close to Bayard Cutting Arboretum State Park, or you can select a more secluded option if you're looking for a relaxing stay. Oakdale is known for its restaurants and shopping. Make sure you have time to check out the beaches while you're in the area.

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

2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment: This holiday home rental outside of Oakdale is located near the beach, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Oakdale?

Expedia has 4 holiday rentals for your stay in Oakdale.

What can I see and do in Oakdale?

Bayard Cutting Arboretum State Park and Connetquot River are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include CM Performing Arts Center and Great South Bay.

What are holiday rentals like in Oakdale?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakdale. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a small group gathering.