A rocky beach with large boulders and a clear view of the ocean.

Smithtown Vacation Rentals

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Our top choices for Smithtown vacation rentals

Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Easy to get to. Listing as described. Bed and furniture are nice and comfy. Only thing I would add is a broom and dust pain and some Clorox wipes so guest can keep it neat. 5 stars! Very nice host. "
United States
Samantha
The price is CA $192
CA $430 total
includes taxes & fees
Jul 7 - Jul 8
Sundown Escape-South Shore Long Island

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (96 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is CA $268
CA $395 total
includes taxes & fees
Jul 29 - Jul 30
DUNE Fairfield Beach

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, (45 reviews)
"This place was the perfect location for us. Almost exact center between Jones beach and Port Jefferson. Clean and identical to what is shown."
United States
Marcus
The price is CA $141
CA $234 total
includes taxes & fees
Jul 12 - Jul 13
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (6 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is CA $89
CA $394 total
includes taxes & fees
Jul 7 - Jul 8
The Royal Suite - Ronkonkoma

Cozy Country Cottage #4

Cozy Country Cottage #4
Miller Place
9.6 out of 10, Exceptional, (16 reviews)
"Great stay"
United States
Susan W.
The price is CA $270
CA $535 total
includes taxes & fees
Jul 7 - Jul 8
Cozy Country Cottage #4

Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (7 reviews)
"The whole experience was great"
United States
David
The price is CA $151
CA $305 total
includes taxes & fees
Jul 12 - Jul 13
Your Perfect Getaway Between Farmingdale & Amityville

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, (16 reviews)
"Cute little apt . Perfect location highly recommend"
United States
Kristin
The price is CA $135
CA $244 total
includes taxes & fees
Jul 7 - Jul 8
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is CA $204
CA $485 total
includes taxes & fees
Jul 7 - Jul 8
Sundown Escape Near SouthShore University Hospital

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, (27 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 CA $204
CA $357 total
includes taxes & fees
Jul 17 - Jul 18
Private 1 bedroom apt in a quiet neighborhood, close to all!

Cozy Country Cottage #2

Cozy Country Cottage #2
Miller Place
9.2 out of 10, Wonderful, (17 reviews)
"Great place to stay, clean, location is close to everything, bed is oh, so comfortable. Love this cottage it is my home away from home. "
United States
Lillian D.
The price is CA $312
CA $591 total
includes taxes & fees
Jul 7 - Jul 8
Cozy Country Cottage #2

South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (5 reviews)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is CA $192
CA $321 total
includes taxes & fees
Jul 7 - Jul 8
South Shore Studio in Mastic

A little Home away from Home

A little Home away from Home
Ronkonkoma
The price is CA $188
CA $247 total
includes taxes & fees
Jul 10 - Jul 11
A little Home away from Home

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 CA $160
CA $484 total
includes taxes & fees
Jul 7 - Jul 8
Spacious one Bedroom Apt with private entrance

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 CA $234
CA $764 total
includes taxes & fees
Jul 8 - Jul 9
Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Charming RV in friendly Bethpage

Charming RV in friendly Bethpage
Bethpage
The price is CA $192
CA $425 total
includes taxes & fees
Jul 19 - Jul 20
Charming RV in friendly Bethpage

Family-Friendly Retreat w/ Trampoline & Grill

Family-Friendly Retreat w/ Trampoline & Grill
Locust Valley
6.0 out of 10, (1 review)
The price is CA $213
CA $596 total
includes taxes & fees
Jul 7 - Jul 8
Family-Friendly Retreat w/ Trampoline & Grill

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 CA $277
CA $545 total
includes taxes & fees
Jul 7 - Jul 8
Luxe Provincial Style Studio w/ Patio & Parking

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
The price is CA $291
CA $563 total
includes taxes & fees
Jul 7 - Jul 8
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is CA $306
CA $490 total
includes taxes & fees
Jul 22 - Jul 23
Spacious 3BR Family Home Near Everything

1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.6 out of 10, Excellent, (23 reviews)
"Well suited for our needs."
United States
Teresa D.
The price is CA $166
CA $281 total
includes taxes & fees
Jul 8 - Jul 9
1 bedroom 1 bath private entrance
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . Seeing all the best attractions is bound to make you fall in love with Smithtown. Who knows, you may even be tempted to extend your vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Smithtown?

Yes, there are vacation rentals in Smithtown close to Blydenburgh County Park, or you can choose a more remote option if you're looking for extra privacy while you relax. Smithtown is known for its lake views.

What are some of the best vacation home rentals in Smithtown?

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. : This vacation home rental outside of Smithtown has air-conditioning and a Smart TV 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?

Family-friendly attractions include Blydenburgh County Park, whereas Nissequogue River is a spot to enjoy the outdoors. Stonebridge Golf Links and Country Club and Caleb Smith State Park are other places to visit while you're in town.

What are vacation rentals like in Smithtown?

Vacation rentals are private properties you can book for a couple days or more in Smithtown. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.