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

Smithtown Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Smithtown vacation rentals

Terrace/patio

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is ￥35,327
￥56,580 total
includes taxes & fees
Aug 18 - Aug 19
Spacious 3BR Family Home Near Everything
Deluxe Apartment, Non Smoking, Private Bathroom | Interior

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 ￥22,397
￥49,922 total
includes taxes & fees
Jul 27 - Jul 28
Sundown Escape-South Shore Long Island
Apartment (4 Bedrooms) | Interior

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

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
Classic Suite | Iron/ironing board, WiFi (free), bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (100 reviews)
"Staff is excellent very clean and comfortable. Nice pla e with great beach access!"
United States
Stacie
The price is ￥31,497
￥46,214 total
includes taxes & fees
Aug 25 - Aug 26
DUNE Fairfield Beach
Standard Room, 1 King Bed, Main Building | Property entrance

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
The price is ￥57,345
￥65,947 total
includes taxes & fees
Jul 29 - Jul 30
Guesthouse at Norwalk Inn
House | 4 bedrooms, high-speed internet

Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is ￥143,195
￥207,631 total
includes taxes & fees
Aug 19 - Aug 20
Stareway to Heaven in Fairfield
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

Inn at Jericho

Inn at Jericho

8/10 Good
"The staff at the Inn at Jericho was great...very efficient and accommodating. The room was clean, but the property is showing signs of age. All the room amenities worked, but the mattress was a bit saggy, the television monitor was a bit dim, and the air-conditioning unit was rather noisy. The location is easy to find, and the area seems safe. While there is no breakfast, there are breakfast options within easy walking distance, with a McDonald's right next door and a short walk to a Dunkin. There are many dining options within driving distance. Overall, this is an okay choice for a no-frills, budget-minded stay."
David 2-night trip
Posted 6 hours ago
Inn at Jericho

Find out more about Smithtown

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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?

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.