Holbrook Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Holbrook

Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
8.8 out of 10, Excellent, (13)
"4 families came from CA for a graduation celebration. Enough room and beds for all 10 of us. Easy access to lake. Backyard is huge, had fun playing badminton and volleyball. Also lit a fire at the fire pit one night. Managers were very responsive to our questions and requests There is a projector and we were able to watch movies at night. Pretty cool. Had a great stay."
The price is NZ$1,671
per night
1 Jun - 2 Jun
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
The President's Mansion Stunning 7-Bedroom 4 Bath
The President's Mansion Stunning 7-Bedroom 4 Bath
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
9.4 out of 10, Exceptional, (9)
"It’s was perfect for what I needed. A comfortable place to sleep and a hot shower. The room was perfectly appointed also. I would recommend and stay there again. "
The price is NZ$241
per night
6 Jun - 7 Jun
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Save an average of 15% on thousands of hotels when you're signed in
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly
8.4 out of 10, Very good, (5)
"We found the house to be really cute and fun to stay in. The location was excellent and we even saw a deer on our last morning! Our main issues, and why this isn’t a 5 star rating, were that multiple lighting fixtures weren’t working and there was an entire bed missing. The ad mentions “1 queen, 1 double, 4 twin’ beds however there’s really 1 queen and 4 twins. This could have caused a big problem if our group was just a bit larger. The ad should be changed to reflect the accurate information...
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
The price is NZ$730
per night
9 Jun - 10 Jun
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
1 bedroom 1 bath private entrance
9.6 out of 10, Exceptional, (8)
"Neat, clean & quite"
The price is NZ$326
per night
11 Jun - 12 Jun
1 bedroom 1 bath private entrance
NEW 7-Bedrm House w/Pool, Swim-Up Bar, Grill, Pool Table, Fitness room/play room
10.0 out of 10, Exceptional, (3)
"We spent a wonderful Thanksgiving together under one roof. The house was spacious enough to accommodate 11 adults, two very active kids, teenagers who needed private time and a baby. It was well stocked with everything one would need to entertain such a large party, we just had to supply the food and drink. The manager, Johanna was very responsive to all of my questions. We will definitely consider coming back and or renting a different home with this group. The one snafu was that 2 out of the 4...
NEW 7-Bedrm House w/Pool, Swim-Up Bar, Grill, Pool Table, Fitness room/play room
One Bedroom Apt. in Ocean Bay Park with deck & gas grill
9.4 out of 10, Exceptional, (31)
"It’s our fourth year in a row…and we’ll be back."
One Bedroom Apt. in Ocean Bay Park with deck & gas grill
Dog-friendly home just blocks from the bay with deck & private hot tub
8.4 out of 10, Very good, (17)
"The house was clean. Communication with management company was subpar. We got scripted responses to all questions, and false information. For example, we asked if hot tub was working and was told it was. When we arrived, the hot tub was broken and dirty. Also, check-out is at 10am and there is nowhere to leave belongings if you’d like to stay in FI for the day. They should allow a place to keep luggage prior to departure. Overall, great and clean house and amazing location!"
Dog-friendly home just blocks from the bay with deck & private hot tub
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
10.0 out of 10, Exceptional, (46)
"Traveling with family and dog... private walk to the beach, stylish but simple, comfortable beds, clean and organized, responsive management... 2 bedrooms downstairs, one entire 2nd floor master bedroom / entertaining space upstairs, and an attached 'cottage' king studio that is attached to the main house."
Westhampton Beach Oceanfront, 4 Bedrooms, Pool. Super Clean. Relax and Chill.
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters
10.0 out of 10, Exceptional, (49)
"Beautiful home in a great location with a wonderful view. Thoughtfully designed, furnished and stocked with everything you'll need. Also, great communication from the owners! Spent the weekend with teens and can't wait to return for a more relaxing adult trip!"
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
8.0 out of 10, Very good, (37)
"The property was misrepresented and unsafe. My parents didnt stay with us due to conditions of the property. We contacted Vacasa the rental management company and decided to leave the property and stay with friends as the windows were broken and shattered and the master bed was broken, no wifi, no functional washer and the list goes on. I expect a full refund from VRBO....I am a frequent client of VRBO and this was not acceptable. Please advise how to go about obtaining a full refund or I will...
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
10.0 out of 10, Exceptional, (9)
"My wife, two children (28, 30) and I came to town for a couple of family events and stayed 11 days. If I had to sum up our time in a single word, I would use "Wonderful"! The check-in process was a breeze. The open floor plan made it feel like you were part of everything going on whether cooking in the kitchen, sitting at the table or on the couch. We spent time every night in the game room shooting pool, playing ping pong and foosball together. The only reason the TV was on at all was for a...
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment
8.6 out of 10, Excellent, (21)
"We had a great time the property looked like the picture minor hiccups"
2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment
Beachfront Romance: Rustic Home w/ Private Beach
9.2 out of 10, Wonderful, (39)
"The house is small but it has everything you need. The ocean was lovely to watch and good scavenging for rocks and sea glass. Very private place. My pup and I had a good time!"
Beachfront Romance: Rustic Home w/ Private Beach
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
The price is NZ$462
per night
30 May - 31 May
Private Waterfront Cottage on Long Islands North Shore Northport Village NY
Private 1 bedroom apt in a quiet neighborhood, close to all!
9.4 out of 10, Exceptional, (11)
"Thank you very much for being so accommodating with our stay! It was very clean, had all the essentials plus extra and we really liked how we had our own private patio. Will definitely be staying again in the future!"
The price is NZ$370
per night
30 May - 31 May
Private 1 bedroom apt in a quiet neighborhood, close to all!
Charming Cape Close to the Ocean
5.2 out of 10, (5)
"Great area and good rental"
Charming Cape Close to the Ocean
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
8.6 out of 10, Excellent, (8)
"The property was clean and large and the outdoor space made for a fun gathering place, especially for the children in our group. It would have been nice to have dedicated spaces to hang towels and clothes, especially as we had so many people staying. The hosts were friendly and accommodating and we would stay again."
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
Beautiful 3 BR Full House w/ King Bed on Dead End- 5 min from town!
9.8 out of 10, Exceptional, (11)
"Great location to visit family on the South Shore. Easy access to town/restaurants. Very responsive host! We’ll be back."
Beautiful 3 BR Full House w/ King Bed on Dead End- 5 min from town!
Don't see what you're looking for?
See all available properties in Holbrook
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.

Other types of properties in Holbrook you may be interested in

Hyatt Regency Long Island
3.5 star property
8.0 out of 10, Very good, (1002)
"I had surgery the of my stay at the hotel. Staff was extremely helpful and accommodating. Room was immaculate. "
The price is NZ$277
per night
30 May - 31 May
Hyatt Regency Long Island
Radisson Hotel Hauppauge-Long Island
3.5 star property
6.0 out of 10, (1003)
"Should have a free breakfast for the price they charged. "
The price is NZ$220
per night
9 Jun - 10 Jun
Radisson Hotel Hauppauge-Long Island
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
2.5 star property
7.0 out of 10, Good, (1002)
"It was ok the only problem I had was the key card had to get numerous cards, there was a problem with the door lock could not get in"
The price is NZ$182
per night
30 May - 31 May
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Holbrook holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Holbrook. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Holbrook. Seeing all the best attractions is bound to make you fall in love with Holbrook. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Holbrook short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Holbrook?

Yes, there are holiday rentals close to the most popular sights in Holbrook, or you can select a more secluded option if you're looking for a relaxing stay. Holbrook is known for its gardens and restaurants. Make sure you have time to check out the shopping while you're in the area.

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

Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres : This holiday home rental outside of Holbrook is located on a lake, 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 games.

What can I see and do in Holbrook?

While exploring the area, visit family-friendly sights like Town of Brookhaven Wildlife and Ecology Center, or get outside and enjoy nature at Lake Ronkonkoma. Suffolk County Community College and Private are a couple of places you'll find in the wider area.

What are holiday rentals like in Holbrook?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Holbrook. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for family gatherings.

Recent reviews of Holbrook properties
Expedia verified reviews