Smithtown Holiday Rentals

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Our top choices for Smithtown holiday rentals

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is AU$479
includes taxes & fees
6 May - 7 May
Spacious 3BR Family Home Near Everything

Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
The price is AU$351
includes taxes & fees
7 May - 8 May
Sundown Escape-South Shore Long Island

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 AU$243
includes taxes & fees
4 May - 5 May
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
7.8 out of 10, Good, (10 reviews)
"The place was great. It was clean and spacious, and located on a quiet street. It was also accessible to all the major roads. The host was very accommodating. Very pleased with it all and would highly recommend! "
United Kingdom
Selective Travel M.
The price is AU$472
includes taxes & fees
4 May - 5 May
Spacious one Bedroom Apt with private entrance

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 AU$314
includes taxes & fees
5 May - 6 May
South Shore Studio in Mastic

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 AU$762
includes taxes & fees
29 May - 30 May
Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Private 1 bedroom apt in a quiet neighborhood, close to all!

Private 1 bedroom apt in a quiet neighborhood, close to all!
Centereach
9.6 out of 10, Exceptional, (26 reviews)
"It was the perfect landing pad for a family reunion. We hope to stay there again next year."
United States
Amanda
The price is AU$349
includes taxes & fees
4 May - 5 May
Private 1 bedroom apt in a quiet neighborhood, close to all!

East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!
East Meadow
8.8 out of 10, Excellent, (15 reviews)
"The apartment was very clean and well maintaimed. This was the perfect property to stay at over the holidays as I grew up in the area and had many moments of nostalgia going to old restaurants and shops I frequented as a kid. "
United States
Alexander A.
The price is AU$228
includes taxes & fees
4 May - 5 May
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (85 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is AU$370
includes taxes & fees
10 May - 11 May
DUNE Fairfield Beach

1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.8 out of 10, Excellent, (22 reviews)
"Well suited for our needs."
United States
Teresa D.
The price is AU$233
includes taxes & fees
5 May - 6 May
1 bedroom 1 bath private entrance

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 AU$753
includes taxes & fees
4 May - 5 May
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.6 out of 10, Exceptional, (7 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is AU$370
includes taxes & fees
4 May - 5 May
Cozy king suite with kitchen and dining area.

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 AU$951
includes taxes & fees
6 May - 7 May
3 Story Beach Waterview, 3 KING bed, golf putting green!

Lovely RV with AC in charming Bethpage a mile from the train to NYC

Lovely RV with AC in charming Bethpage a mile from the train to NYC
Bethpage
7.0 out of 10, Good, (4 reviews)
"Super convenient and the host was very responsive. I highly recommend."
United States
Andrew B.
The price is AU$326
includes taxes & fees
4 May - 5 May
Lovely RV with AC in charming Bethpage a mile from the train to 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 AU$528
includes taxes & fees
4 May - 5 May
Luxe Provincial Style Studio w/ Patio & Parking

The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
10.0 out of 10, Exceptional, (4 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is AU$502
includes taxes & fees
4 May - 5 May
The Royal Suite - Ronkonkoma

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (10 reviews)
"This house was so lovely, clean, cozy, and well-appointed - everything we could have asked for for a girls' weekend! And so close to the town of Westport with its excellent restaurants and shops. The best!"
United States
Rebecca H.
The price is AU$728
includes taxes & fees
4 May - 5 May
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Huntington
9.8 out of 10, Exceptional, (7 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is AU$314
includes taxes & fees
10 May - 11 May
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

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 AU$946
includes taxes & fees
4 May - 5 May
Modern Vacation home. Close to The Hamptons

JC Entire Apartment remodeled, close to Airport and Ferry

JC Entire Apartment remodeled, close to Airport and Ferry
Coram
10.0 out of 10, Exceptional, (3 reviews)
"Would definitely stay again "
United States
Katherine R.
The price is AU$280
includes taxes & fees
19 May - 20 May
JC Entire Apartment remodeled, close to Airport and Ferry
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 Smithtown Hotel Reviews

Find out more about Smithtown

Everything you need to know about Smithtown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Smithtown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Smithtown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Smithtown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Smithtown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Smithtown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Smithtown holiday rentals we have selected for you start as low as AU$228 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Smithtown rentals

At Expedia, we put the best Smithtown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Smithtown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Smithtown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Smithtown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Smithtown?

Yes, there are holiday rentals in Smithtown close to Blydenburgh County Park, or you can select a more secluded option if you're looking for a relaxing stay. Smithtown is known for its lake views.

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

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. : This holiday home rental outside of Smithtown has air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave and a coffee maker.

What can I see and do in Smithtown?

Nissequogue River and Caleb Smith State Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Blydenburgh County Park. Stonebridge Golf Links and Country Club and Avalon Park and Preserve are a couple of places you'll find in the wider area.

What are holiday rentals like in Smithtown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Smithtown. Holiday rentals feature amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for small groups.