Smithtown Vacation Rentals

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Our top choices for Smithtown vacation rentals

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
$213 nightly
The price is $243
May 26 - May 27
Total with taxes and fees
Spacious 3BR Family Home Near Everything

Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
$277 nightly
The price is $316
May 12 - May 13
Total with taxes and fees
Sundown Escape-South Shore Long Island

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (87 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
$233 nightly
The price is $268
May 26 - May 27
Total with taxes and fees
DUNE Fairfield Beach

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.
$200 nightly
The price is $229
May 18 - May 19
Total with taxes and fees
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
$480 nightly
The price is $549
May 29 - May 30
Total with taxes and fees
Shop, Hike, Golf & Swim: Inviting Deer Park Escape

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
$336 nightly
The price is $384
May 17 - May 18
Total with taxes and fees
Luxe Provincial Style Studio w/ Patio & Parking

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
$151 nightly
The price is $173
May 12 - May 13
Total with taxes and fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

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.
$309 nightly
The price is $353
May 12 - May 13
Total with taxes and fees
The Royal Suite - Ronkonkoma

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.
$233 nightly
The price is $266
May 12 - May 13
Total with taxes and fees
Cozy king suite with kitchen and dining area.

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, (76 reviews)
"Location was perfect!"
United States
Linda J P.
$480 nightly
The price is $548
May 18 - May 19
Total with taxes and fees
Captain's Cottage - Cold Spring Harbor Water Views

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.
$474 nightly
The price is $542
May 12 - May 13
Total with taxes and fees
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

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.
$301 nightly
The price is $343
May 17 - May 18
Total with taxes and fees
Spacious one Bedroom Apt with private entrance

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.
$426 nightly
The price is $487
May 12 - May 13
Total with taxes and fees
THE OASIS @ LONG ISLAND

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
8.8 out of 10, Excellent, (10 reviews)
"Had a great stay "
United States
Desiree
$144 nightly
The price is $160
May 14 - May 15
Total with taxes and fees
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

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.
$199 nightly
The price is $227
May 13 - May 14
Total with taxes and fees
South Shore Studio in Mastic

Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.6 out of 10, Exceptional, (4 reviews)
"It was relaxing very comfortable "
United States
Julian R.
$190 nightly
The price is $217
May 12 - May 13
Total with taxes and fees
Your Perfect Getaway Between Farmingdale & Amityville

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.
$615 nightly
The price is $703
May 12 - May 13
Total with taxes and fees
Modern Vacation home. Close to The Hamptons

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.
$600 nightly
The price is $686
May 12 - May 13
Total with taxes and fees
3 Story Beach Waterview, 3 KING bed, golf putting green!

Family-Friendly Retreat w/ Trampoline & Grill

Family-Friendly Retreat w/ Trampoline & Grill
Locust Valley
$372 nightly
The price is $415
May 17 - May 18
Total with taxes and fees
Family-Friendly Retreat w/ Trampoline & Grill

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
$331 nightly
The price is $381
May 13 - May 14
Total with taxes and fees
Guesthouse at Norwalk Inn
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 $162 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?

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

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.