Smithtown Vacation Rentals

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Our top choices for Smithtown vacation rentals

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Smithtown
6.8 out of 10, (3 reviews)
"We enjoyed our stay. The apartment was simple, clean, and comfortable. The neighborhood felt safe, and it was easy to call Uber for rides. LIRR access was also convenient, which made traveling to New York City and Stony Brook very manageable. The highlight was the beautiful backyard, which made the place feel relaxing."
United States
Jing L.
$201 nightly
The price is $230
Feb 13 - Feb 14
Total with taxes and fees
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

Tiny Home Private, Students, Nurses, Tech

Tiny Home Private, Students, Nurses, Tech
Bay Shore
8.6 out of 10, Excellent, (7 reviews)
"We wanted an inexpensive place to stay out on Long Island for July 4th weekend. We were a 15-20 minute drive to the beautiful beaches of Robert Moses and a 2 hour drive from Montauk.We were able to stay for a very reasonable price over a notoriously expensive weekend.Jenelle's communication was direct, welcoming and helpful.We would definitely stay here again!"
United States
Melanie M.
$193 nightly
The price is $202
Feb 14 - Feb 15
Total with taxes and fees
Tiny Home Private, Students, Nurses, Tech

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.
$212 nightly
The price is $237
Feb 13 - Feb 14
Total with taxes and fees
Lovely RV with AC in charming Bethpage a mile from the train to NYC

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (79 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
$232 nightly
The price is $267
Feb 16 - Feb 17
Total with taxes and fees
DUNE Fairfield Beach

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (7 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
$331 nightly
The price is $378
Feb 13 - Feb 14
Total with taxes and fees
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

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.
$470 nightly
The price is $537
Feb 16 - Feb 17
Total with taxes and fees
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (3 reviews)
"Great stay! Super comfy and clean😊"
United States
ERIN
$199 nightly
The price is $227
Feb 13 - Feb 14
Total with taxes and fees
South Shore Studio in Mastic

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (18 reviews)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
$159 nightly
The price is $182
Feb 13 - Feb 14
Total with taxes and fees
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

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, (38 reviews)
"We had a good experience and we brought our little pup and she was welcome there. Clean and quiet stay "
United States
janice s.
$149 nightly
The price is $170
Feb 13 - Feb 14
Total with taxes and fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (28 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
$1,050 nightly
The price is $1,200
Feb 15 - Feb 16
Total with taxes and fees
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

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.
$457 nightly
The price is $522
Mar 10 - Mar 11
Total with taxes and fees
Modern Vacation home. Close to The Hamptons

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
$330 nightly
The price is $380
Feb 14 - Feb 15
Total with taxes and fees
Guesthouse at Norwalk Inn

The Moonrise Motel is a new vacation spot located in the heart of Kismet!

The Moonrise Motel is a new vacation spot located in the heart of Kismet!
Copiague
$703 nightly
The price is $803
Feb 13 - Feb 14
Total with taxes and fees
The Moonrise Motel is a new vacation spot located in the heart of Kismet!

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (74 reviews)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
$411 nightly
The price is $470
Feb 16 - Feb 17
Total with taxes and fees
Captain's Cottage - Cold Spring Harbor Water Views

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
9.2 out of 10, Wonderful, (9 reviews)
"Nice location, clean and comfortable, and looking forward to possibly revisiting."
United States
Doug S.
$140 nightly
The price is $156
Feb 19 - Feb 20
Total with taxes and fees
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

THE OASIS @ LONG ISLAND

THE OASIS @ LONG ISLAND
Huntington Station
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
$423 nightly
The price is $483
Feb 28 - Mar 1
Total with taxes and fees
THE OASIS @ LONG ISLAND

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)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! "
United States
Red F.
$601 nightly
The price is $687
Feb 24 - Feb 25
Total with taxes and fees
3 Story Beach Waterview, 3 KING bed, golf putting green!

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Commack
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay"
United States
Kenneth B.
$600 nightly
The price is $685
Feb 15 - Feb 16
Total with taxes and fees
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

1-bedroom apartment with AC in Syosset

1-bedroom apartment with AC in Syosset
Syosset
$393 nightly
The price is $439
Feb 19 - Feb 20
Total with taxes and fees
1-bedroom apartment with AC in Syosset

2-bedroom apartment in delightful 4 minutes away from Babylon village

2-bedroom apartment in delightful 4 minutes away from Babylon village
West Babylon
$239 nightly
The price is $273
Feb 13 - Feb 14
Total with taxes and fees
2-bedroom apartment in delightful 4 minutes away from Babylon village
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Smithtown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Smithtown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Smithtown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $156 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Smithtown rentals

At Expedia, we put the best Smithtown vacation 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 vacation.

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 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?

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.: This vacation home rental outside of Smithtown is located by the ocean and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a pool table, and a hot tub so you can immerse yourself in your vacation.

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 Smithaven Mall are a couple of places you'll find in the larger area.

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.