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

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
$270 nightly
The price is $311
Jul 28 - Jul 29
Total with taxes and fees
DUNE Fairfield Beach

Charming Rocky Point Home ~ 1 Mi to Beach!

Charming Rocky Point Home ~ 1 Mi to Beach!
3.0 star property
Rocky Point
$540 nightly
The price is $616
Jul 19 - Jul 20
Total with taxes and fees
Charming Rocky Point Home ~ 1 Mi to Beach!

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
$261 nightly
The price is $298
Jul 7 - Jul 8
Total with taxes and fees
Sundown Escape-South Shore Long Island

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, (80 reviews)
"Location was perfect!"
United States
Linda J P.
$629 nightly
The price is $719
Jul 7 - Jul 8
Total with taxes and fees
Captain's Cottage - Cold Spring Harbor Water Views

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
$221 nightly
The price is $252
Jul 28 - Jul 29
Total with taxes and fees
Spacious 3BR Family Home Near Everything

Peaceful private 2-bedroom house in Bayport. Amazing location!

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
9.4 out of 10, Exceptional, (6 reviews)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
United States
Emily D.
$463 nightly
The price is $529
Jun 28 - Jun 29
Total with taxes and fees
Peaceful private 2-bedroom house in Bayport. Amazing location!

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.
$602 nightly
The price is $688
Jun 28 - Jun 29
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, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
$319 nightly
The price is $367
Jul 7 - Jul 8
Total with taxes and fees
Guesthouse at Norwalk Inn

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, (44 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
$144 nightly
The price is $165
Jul 1 - Jul 2
Total with taxes and fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

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.
$478 nightly
The price is $546
Jun 29 - Jun 30
Total with taxes and fees
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

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, (29 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
$1,274 nightly
The price is $1,456
Jul 5 - Jul 6
Total with taxes and fees
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Waterfront house next to Bellport golf course

Waterfront house next to Bellport golf course
East Patchogue
10.0 out of 10, Exceptional, (16 reviews)
"Our stay was wonderful! Everything was clean and the host was very flexible. We would definitely come again for the summer time"
United States
Depp S.
$1,317 nightly
The price is $1,504
Jul 7 - Jul 8
Total with taxes and fees
Waterfront house next to Bellport golf course

Production Studio - 4 Sets / 2 Offices / Light Bank / Hex Lighting - 4k SF

Production Studio - 4 Sets / 2 Offices / Light Bank / Hex Lighting - 4k SF
West Babylon
$1,085 nightly
The price is $1,240
Jul 1 - Jul 2
Total with taxes and fees
Production Studio - 4 Sets / 2 Offices / Light Bank / Hex Lighting - 4k SF

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.
$349 nightly
The price is $399
Jul 8 - Jul 9
Total with taxes and fees
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Tranquil Stay

Tranquil Stay
Shirley
8.0 out of 10, Very Good, (10 reviews)
"Great stay! "
United States
Emily S.
$643 nightly
The price is $734
Jul 5 - Jul 6
Total with taxes and fees
Tranquil Stay

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, (23 reviews)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
$752 nightly
The price is $859
Jul 7 - Jul 8
Total with taxes and fees
3 Story Beach Waterview, 3 KING bed, golf putting green!

Bright airy Fair Harbor home with ocean views steps from the soft sandy beach

Bright airy Fair Harbor home with ocean views steps from the soft sandy beach
Fire Island
9.6 out of 10, Exceptional, (4 reviews)
"Perfect Fire Island getaway. Great location and beautiful beach home. Would recommend and love to come back!"
United States
Jessica W.
$1,142 nightly
The price is $1,305
Jun 29 - Jun 30
Total with taxes and fees
Bright airy Fair Harbor home with ocean views steps from the soft sandy beach

Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
$1,194 nightly
The price is $1,373
Jul 12 - Jul 13
Total with taxes and fees
Stareway to Heaven in Fairfield

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, (12 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.
$724 nightly
The price is $820
Jul 12 - Jul 13
Total with taxes and fees
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

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
$199 nightly
The price is $228
Jun 29 - Jun 30
Total with taxes and fees
Your Perfect Getaway Between Farmingdale & Amityville
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 $165 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.

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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 Home Located Close to Stony Brook!: This vacation home rental outside of Smithtown offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.