Photo by Dawn Biscardi Alperstein

Oakdale Holiday Rentals

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Check prices for these dates

Tonight
8 Apr - 9 Apr
Tomorrow
9 Apr - 10 Apr
This weekend
11 Apr - 13 Apr
Next weekend
18 Apr - 20 Apr

Holiday Rentals in Oakdale

Luxury and Affordable Family Home
Interior

Luxury and Affordable Family Home

10.0 out of 10, Exceptional, (2)
"My family and I had the pleasure of staying here during the Christmas holidays, and it was an excellent experience. We were especially grateful for the accessibility features, as my grandmother (85 years young), who uses a walker and had recently undergone surgery, was able to comfortably stay on the main floor. The property had just a few steps to enter, and best of all, there was a bedroom and full bathroom on the main level, along with ample room for a walker or wheelchair.The home itself was...
The price is HK$2,408
HK$5,938 total
includes taxes & fees
20 Apr - 21 Apr
Luxury and Affordable Family Home
East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries
Miscellaneous

East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries

10.0 out of 10, Exceptional, (84)
"Place was beautiful. It was very clean. Easy to get to. Would stay again"
The price is HK$1,748
HK$3,914 total
includes taxes & fees
9 Apr - 10 Apr
East End cottage on water!Pet Friendly! Wood FP Minutes from Hamptons & wineries
fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc
Smart TV, books

fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

10.0 out of 10, Exceptional, (11)
"The property was as advertised. It was clean and there was plenty of room for my family of 4. The place is updated and has large tvs in each room. We all agreed that beds were awesome and made for a great nights sleep. The location was close to major highways, making it easy to get anywhere we needed to go. I would definitely stay here again. Thank you for a great stay!."
fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc
Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private
Exterior

Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private

10.0 out of 10, Exceptional, (75)
"Just as pictured. Beautiful spotless.The backyard is to die for. Loved the Toto toilet and shower was great. Make sure to walk down to the dock. One thing to bear in mind is lots of steps. I’m having knee surgery so it was a little difficult for me but I knew the steps would be there so that’s no reflection on the house. You will love your stay here. I guarantee it.the toy toilet and the shower is beautiful"
Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private
Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment
Exterior

Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment

10.0 out of 10, Exceptional, (15)
"We recently had the joy of staying here with family meeting from different parts of New York and New Jersey. House is beautiful, location is quiet and peaceful with a great view of the bay. Nearby to some great Long Island beaches. Loved the pool and amenities of the home. Faraz was an excellent host and extremely responsive to our needs "
The price is HK$6,788
HK$16,252 total
includes taxes & fees
17 Apr - 18 Apr
Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment
The Raabbit Hole
Fridge, microwave, oven, stovetop

The Raabbit Hole

9.2 out of 10, Wonderful, (22)
"Only recommendation would be to upgrade the beach chairs . The house was very Homie and comfortable and plenty big. Would definitely stay again. "
The Raabbit Hole
1856 Trading House w/ walk to water
Smart TV, DVD player, books

1856 Trading House w/ walk to water

9.6 out of 10, Exceptional, (41)
"It was clean and just what we needed the calling fan didn't work but the AC did so no real deal breaker"
1856 Trading House w/ walk to water
Beach Apt. Wineries, Shopping, Dining
Property grounds

Beach Apt. Wineries, Shopping, Dining

6.0 out of 10, (11)
"It was a decent place to stay."
The price is HK$1,204
HK$2,565 total
includes taxes & fees
9 Apr - 10 Apr
Beach Apt. Wineries, Shopping, Dining
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
Beautiful Private Studio Apartment!
Outdoor dining

Beautiful Private Studio Apartment!

9.6 out of 10, Exceptional, (5)
"we enjoyed our stay."
Beautiful Private Studio Apartment!
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
2 bedroom apartment minutes away from Gambling, Bars, Restaurants, Water Park...
Fridge, microwave, stovetop, coffee/tea maker

2 bedroom apartment minutes away from Gambling, Bars, Restaurants, Water Park...

8.4 out of 10, Very good, (9)
"If your looking for a place to get away from everyday life and just relax. This is your place. I would definitely come back again."
2 bedroom apartment minutes away from Gambling, Bars, Restaurants, Water Park...
Captain's Cottage - Cold Spring Harbor Water Views
Aerial view

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (57)
"Great home to stay. Beautiful area to explore!"
The price is HK$1,508
HK$3,509 total
includes taxes & fees
9 Apr - 10 Apr
Captain's Cottage - Cold Spring Harbor Water Views
3 Story Beach Waterview, 3 KING bed, golf putting green!
Aerial view

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

10.0 out of 10, Exceptional, (15)
"We stayed on Long Island for 4 nights to coach a Perfect Game Baseball Tournament. This property was spacious enough to host my wife and I along with 4 other coaches (6 adults total). We were also able to bring our two jack russells with us. We had a great time, and look forward to staying here again."
The price is HK$1,158
HK$4,441 total
includes taxes & fees
9 Apr - 10 Apr
3 Story Beach Waterview, 3 KING bed, golf putting green!
Gatsby's - Heated Plunge Pool & Hot Tub in OBP, Sleeps 24, Steps From The Beach
Property grounds

Gatsby's - Heated Plunge Pool & Hot Tub in OBP, Sleeps 24, Steps From The Beach

Gatsby's - Heated Plunge Pool & Hot Tub in OBP, Sleeps 24, Steps From The Beach
Kismet, Fire Island 4 bedroom family house "IMAGINE"
Property grounds

Kismet, Fire Island 4 bedroom family house "IMAGINE"

9.8 out of 10, Exceptional, (22)
"To quote my son, our stay at Imagine was a “top-tier week”! Everything was perfect and as described. We thoroughly enjoyed the incredible kitchen and outside deck. Fran was helpful and attentive, a wonderful host. Our family was happy and comfortable all week. Thank you to the Cintorino Family for sharing your home with our family 💙"
Kismet, Fire Island 4 bedroom family house "IMAGINE"
Cozy 1-bedroom apartment with WiFi, AC in peaceful North Babylon
1 bedroom, WiFi

Cozy 1-bedroom apartment with WiFi, AC in peaceful North Babylon

The price is HK$878
HK$1,846 total
includes taxes & fees
9 Apr - 10 Apr
Cozy 1-bedroom apartment with WiFi, AC in peaceful North Babylon
Cozy Country Cottage #3
Interior

Cozy Country Cottage #3

10.0 out of 10, Exceptional, (15)
"This is our second time and the cottages are well equipped with everything you need. They are very cozy, we especially enjoyed the fireplace/heater in the cool evenings."
The price is HK$1,165
HK$2,512 total
includes taxes & fees
9 Apr - 10 Apr
Cozy Country Cottage #3
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
Spacious Home Located Close to Stony Brook!
Property grounds

Spacious Home Located Close to Stony Brook!

6.8 out of 10, (15)
"Great stay great people great costumer care definitely reccomend"
Spacious Home Located Close to Stony Brook!
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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Other types of properties in Oakdale you may be interested in

Hampton Inn Long Island-Brookhaven
Gazebo

Hampton Inn Long Island-Brookhaven

2.5 star property
8.8 out of 10, Excellent, (1046)
"My son and I absolutely loved the pool! "
The price is HK$802
HK$916 total
includes taxes & fees
16 Apr - 17 Apr
Hampton Inn Long Island-Brookhaven
Hyatt Regency Long Island
Exterior

Hyatt Regency Long Island

3.5 star property
8.2 out of 10, Very good, (1008)
"Great experience "
The price is HK$924
HK$1,056 total
includes taxes & fees
20 Apr - 21 Apr
Hyatt Regency Long Island
Holiday Inn Express Hauppauge by IHG
Exterior

Holiday Inn Express Hauppauge by IHG

2.5 star property
8.2 out of 10, Very good, (1013)
"Good "
The price is HK$948
HK$1,083 total
includes taxes & fees
20 Apr - 21 Apr
Holiday Inn Express Hauppauge by IHG
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?

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms: This holiday home rental outside of Oakdale is located near the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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 Great South Bay are a couple of lovely local spots to get outside and enjoy nature. Connetquot River 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.