Photo by Dawn Biscardi Alperstein

Oakdale Holiday Rentals

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Holiday Rentals in Oakdale

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bedroom, iron/ironing board, WiFi, bed sheets

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

9.4 out of 10, Exceptional, (19)
"I really enjoyed my stay. It was convenient and exceeded my expectations. When I am in town again I will definitely book again."
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Fridge, microwave, oven, stovetop

Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

9.4 out of 10, Exceptional, (8)
"Space was nice. Need top sheets on beds. Noisy location and basement tenant."
The price is AU$719
includes taxes & fees
2 Jan - 3 Jan 2025
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Captain's Cottage - Cold Spring Harbor Water Views
Aerial view

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (53)
"Cute, well-appointed house, great communication, fun stay!"
The price is AU$730
includes taxes & fees
7 Jan - 8 Jan 2025
Captain's Cottage - Cold Spring Harbor Water Views
Beautiful Beach House with Large Swimming Pool in Ocean Beach
Smart TV, books, stereo, printers

Beautiful Beach House with Large Swimming Pool in Ocean Beach

10.0 out of 10, Exceptional, (34)
"Wonderful vacation! House has everything you need and the location is perfect. Hosts are quick to respond to any questions. Would definitely stay here again!"
Beautiful Beach House with Large Swimming Pool in Ocean Beach
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

8.8 out of 10, Excellent, (9)
"Clean, spacious home with an amazing pool in a quiet neighborhood. If you're looking for a quiet getaway a good choice!"
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
1 bedroom 1 bath private entrance
1 bedroom, WiFi, bed sheets

1 bedroom 1 bath private entrance

9.0 out of 10, Wonderful, (16)
"Place was very clean and well maintained. Host was extremely helpful and communicative! 10/10 would recommend "
The price is AU$321
includes taxes & fees
28 Dec - 29 Dec
1 bedroom 1 bath private entrance
The President Mansion Luxurious 7BR Family Retreat
Interior

The President Mansion Luxurious 7BR Family Retreat

9.6 out of 10, Exceptional, (5)
"Large enough to sleep 12 adults and 8 children without difficulty! The game room for kids is fabulous and the master bath was a dream come true! Will stay again when visiting Long Island. May plan a summer beach week since so close to Beaches on the South Shore."
The President Mansion Luxurious 7BR Family Retreat
Waterfront Cottage cute and cozy
Interior

Waterfront Cottage cute and cozy

9.4 out of 10, Exceptional, (95)
"We had a great experience staying at this cozy cottage! It was a cottage experience and it exceeded expectations. Communication with the host was smooth and prompt, making the booking process easy! "
Waterfront Cottage cute and cozy
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
Fridge, microwave, oven, stovetop

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

8.2 out of 10, Very good, (44)
"This house was very nice, as pictured or better. Clean, no issues checking in or out. Wagon was there as promised, more bikes than promised, lots of beach towels and chairs provided. The house had two wonderful outdoor second story decks with great views of the water and the ferry dock. Location was perfect, so convenient to ferry and market. Two things not great. Although it had an AC unit in every bedroom that all worked fine which made ground floor cool and comfortable, the main living...
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Private kitchen

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

10.0 out of 10, Exceptional, (23)
"Overall, this was a great stay. The house was clean and as advertised. The location was perfect for us as we were visiting family in Lake Grove, Stonybrook, and Port Jeff. A few recommendations for minor improvements: more towel bars/hooks in the bathroom and an upgraded coffee maker. Regardless, we would happily stay here again when visiting Long Island. "
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Bay-view apartment with deck, grill, enclosed porch, full kitchen, & WiFi
Aerial view

Bay-view apartment with deck, grill, enclosed porch, full kitchen, & WiFi

7.6 out of 10, Good, (9)
"The home is wonderful in a great location. Only if that location was known to the rental company. It may be a google problem, but someone needs to pin the correct location, otherwise you wind up on the wrong ferry, in the wrong town. "
Bay-view apartment with deck, grill, enclosed porch, full kitchen, & WiFi
One Bedroom Apt. in Ocean Bay Park with deck & gas grill
Fridge, microwave, oven, stovetop

One Bedroom Apt. in Ocean Bay Park with deck & gas grill

9.4 out of 10, Exceptional, (36)
"Property is cozy and quaint just large enough for two people.The wifi code in the email and posted in the property were different. We expected a call back from the property manager but never got it. The weather was fantastic."
One Bedroom Apt. in Ocean Bay Park with deck & gas grill
1856 Trading House close to water
Outdoor dining

1856 Trading House close to water

9.4 out of 10, Exceptional, (12)
"Has character, cute. I did hit my head on the Murphy bed, we needed trash bags and forks. Really enjoyed the outdoors fire pit, needed lots of bug spray. Comfortable AC, wish the Bathroom was bigger, kitchen was great."
1856 Trading House close to water
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, (5)
"This was a perfect home base for my short visit to Long Island! It has everything necessary, was close to so many restaurants of all types and the host provided extensive information about the area. The host was communicative and friendly. An overall great stay!"
Walkable to all in Downtown Seaford! Clean 1 bed basement unit
Updated home in great location with spacious living & outdoor features
TV, DVD player

Updated home in great location with spacious living & outdoor features

8.8 out of 10, Excellent, (54)
"We got to the house and it was a lovely house, in a great location. The garbage outside had meat and other garbage not in bags. The storm door was broken which we fixed ourselves, the floor was full of sand, the air conditioner in the kitchen didnt blow cold air and the fan in the ktchen didnt work either, the remote was nowhere to be found. I think some of our money should be refunded."
Updated home in great location with spacious living & outdoor features
Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs
Terrace/patio

Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

9.6 out of 10, Exceptional, (99)
"Perfect location for nearby wedding (Old Field Club in East Setauket) and for places to shop and explore. Beautiful view , comfortable for the 6 of us. Would stay there again."
Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs
2 min away from train station
View from property

2 min away from train station

9.6 out of 10, Exceptional, (5)
" ."
The price is AU$491
includes taxes & fees
2 Jan - 3 Jan 2025
2 min away from train station
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly
Interior

Charming home close to beach with fast WiFi & washer/dryer - dog-friendly

7.6 out of 10, Good, (9)
"It was as cute as it looked on-line and gave us a great space for hanging out and enjoying each other's company. That said, I would recommend that you rent this with loved ones as privacy is limited because of the indoor design. With no insulation or dry wall every noise is heard throughout the house! Other nice surprises: new AC units (very quiet), very comfortable beds, and an outdoor shower with good light. The street is very quiet. I was surprised that basic kitchen supplies weren't included...
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly
Dog-friendly home just blocks from the bay with deck & private hot tub
TV

Dog-friendly home just blocks from the bay with deck & private hot tub

8.0 out of 10, Very good, (24)
"We loved the location, but the home was loaded with spiders, most appliances did not work (dishwasher did not work, blender, toaster oven, the stove top only half worked) - plus the pots were scratched (and with Teflon not useable) The shower door was broken and would not close, the toilet paper roll holder had no dowel to hold roll, toilet seat very loose, door frames were chipped and dirty, hold in wall next the bed in room with bunkbeds, laundry closet had missing doors. "
Dog-friendly home just blocks from the bay with deck & private hot tub
Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome
TV, fireplace

Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome

6.2 out of 10, (14)
"We all had an amazing time. Convenience to the beach was a bonus. Spectacular views of the ocean n the bay. Plenty of space , screen doors were annoying ( but I also live on the beach and understand how beat up everything gets). Would definitely rent this house again."
Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome
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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3.5 star property
6.0 out of 10, (1001)
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The price is AU$193
includes taxes & fees
29 Dec - 30 Dec
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Gazebo

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"Love it"
The price is AU$208
includes taxes & fees
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Days Inn by Wyndham Woodbury Long Island
In-room safe, desk, blackout curtains, iron/ironing board

Days Inn by Wyndham Woodbury Long Island

2.5 star property
7.2 out of 10, Good, (1001)
"Sketchy "
The price is AU$206
includes taxes & fees
29 Dec - 30 Dec
Days Inn by Wyndham Woodbury Long Island
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.

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?

20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.: This holiday home rental outside of Oakdale offers an outdoor pool, a fireplace and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a microwave and kitchenware, so that you can cook with friends or family.

How many holiday rentals are there in Oakdale?

Expedia has 5 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. Great South Bay and Heckscher State Park are a couple of places you'll find in the wider area.

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.