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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Smithtown vacation rentals

A bedroom with a bed, a bedside table, a nightstand, a window with curtains, a door, and a bathroom with a toilet, sink, and towel rack.

1. 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, (56 reviews)
"This stay was very clean and easy. The check-in process was efficient. Thank you, I would definitely book again for a short stay!"
United States
Jaelyn
The price is ￥15,516
￥25,788 total
includes taxes & fees
Oct 25 - Oct 26
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
A wooden deck with a white railing, a stone pathway, and a white fence in the background.

2. Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is ￥27,037
￥46,406 total
includes taxes & fees
Oct 29 - Oct 30
Spacious 3BR Family Home Near Everything
A two-story house with a front porch, a small garden with various plants, and a tree with red leaves.

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

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
9.4 out of 10, Exceptional, (35 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is ￥21,177
￥30,774 total
includes taxes & fees
Nov 10 - Nov 11
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
A house with a paved pathway leading to the front door, surrounded by a well-maintained lawn and various plants.

4. Central 2BR, Garden Suite, Top Amenities & Care!

Central 2BR, Garden Suite, Top Amenities & Care!
Central Islip
10.0 out of 10, Exceptional, (3 reviews)
"Great stay, clean and inviting space. Thanks for a great space away from home; will definietly book again."
United States
Vladamir R.
The price is ￥23,980
￥82,550 total
includes taxes & fees
Nov 3 - Nov 4
Central 2BR, Garden Suite, Top Amenities & Care!
A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

5. 4 BR house by Stony Brook University & Hospital

4 BR house by Stony Brook University & Hospital
Stony Brook
10.0 out of 10, Exceptional, (1 review)
"I left 5* because communication with host was superb. Unfortunately, we did not get to stay there due an issue on our end. From what I experienced with the host and the pictures, I have no reason to believe the home would've been less than perfect. Top notch host and I thank him for always being in touch, from before we supposed to be there, all the way thru, he made sure to reach out."
United States
Joseph L.
The price is ￥66,709
￥148,085 total
includes taxes & fees
Oct 25 - Oct 26
4 BR house by Stony Brook University & Hospital
A wooden deck with outdoor furniture and a white fence.

6. Bright & Comfortable Home in the Heart of It All

Bright & Comfortable Home in the Heart of It All
Central Islip
8.8 out of 10, Excellent, (3 reviews)
"My stay was amazing! The place was bigger in person than i expected, which was such a pleasant surprise. The house was spotless and very clean, making me feel comfortable from the moment I arrived. The host was incredibly helpful, responsive, and made the entire experience smooth and stress-free. I enjoyed my stay and would absolutely book this home again. Highly recommend to anyone looking for a clean, spacious, and welcoming place to stay!"
United States
Tatiana J.
The price is ￥28,801
￥80,220 total
includes taxes & fees
Nov 16 - Nov 17
Bright & Comfortable Home in the Heart of It All
A hot tub with water jets, a television displaying a beach scene, and a sign on the wall.

7. 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, (14 reviews)
"Wonderful stay"
United States
Kenneth B.
The price is ￥125,384
￥204,313 total
includes taxes & fees
Nov 5 - Nov 6
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
A bedroom with a bed, bedside tables, a mirror, a bench, and a wall sign.

8. 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 ￥20,735
￥46,967 total
includes taxes & fees
Oct 29 - Oct 30
Sundown Escape-South Shore Long Island
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

9. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (115 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is ￥27,810
￥41,542 total
includes taxes & fees
Oct 29 - Oct 30
DUNE Fairfield Beach
Exterior

10. Welcoming 1 bedroom apartment in beautiful harbor village.

Welcoming 1 bedroom apartment in beautiful harbor village.
Northport
10.0 out of 10, Exceptional, (1 review)
"Beautiful clean upstairs apartment with a private entrance. Very quiet neighborhood with a small park across the street. Karen, the homeowner who lives downstairs is a wonderful person. The place was perfect for what I needed amd the location was great."
United States
Sallyann S.
The price is ￥29,763
￥49,226 total
includes taxes & fees
Oct 28 - Oct 29
Welcoming 1 bedroom apartment in beautiful harbor village.
A covered outdoor seating area with a white door, a 'No Smoking' sign, and string lights.

11. The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
9.8 out of 10, Exceptional, (10 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is ￥18,478
￥54,955 total
includes taxes & fees
Oct 26 - Oct 27
The Royal Suite - Ronkonkoma
Kitchen | Electric Kettle | Toaster | Blender

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

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
Deer Park
10.0 out of 10, Exceptional, (3 reviews)
"My family and I really enjoyed this property! The host was welcoming, the property was clean and well-cared for, and it’s in a very nice area. We would stay again next time we’re in Long Island!"
United States
Danielle M.
The price is ￥13,177
￥78,504 total
includes taxes & fees
Oct 28 - Oct 29
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
A living room with a brown sofa, a glass coffee table with decorative items, and a kitchen in the background with wooden cabinets and a black refrigerator.

13. Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
8.2 out of 10, Very good, (12 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 ￥17,632
￥53,807 total
includes taxes & fees
Oct 25 - Oct 26
Spacious one Bedroom Apt with private entrance
A modern kitchen with dark cabinetry, a microwave, and a stove. There is a large flat-screen TV mounted on the wall.

14. 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, (10 reviews)
"Great location and cozy studio."
United States
Joseph F.
The price is ￥30,433
￥60,039 total
includes taxes & fees
Oct 25 - Oct 26
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
A compact kitchen with dark cabinets, stainless appliances, and a tiled floor.

15. 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, (29 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 ￥22,569
￥39,754 total
includes taxes & fees
Oct 25 - Oct 26
Private 1 bedroom apt in a quiet neighborhood, close to all!
A living room with a sofa, a coffee table, a mirror, and a patterned rug.

16. Historic Home near Stony Brook Village & Beach

Historic Home near Stony Brook Village & Beach
Stony Brook
7.4 out of 10, Good, (3 reviews)
"V1 church was nearby "
United States
david w.
The price is ￥66,709
￥128,009 total
includes taxes & fees
Oct 27 - Oct 28
Historic Home near Stony Brook Village & Beach
A bedroom with a bed, a bedside lamp, a TV, and a door leading to another room.

17. Cozy 1-bedroom apartment in charming Centereach with AC

Cozy 1-bedroom apartment in charming Centereach with AC
Centereach
The price is ￥20,453
￥26,951 total
includes taxes & fees
Oct 25 - Oct 26
Cozy 1-bedroom apartment in charming Centereach with AC
A modern bedroom with a large bed, a bedside table, a sofa, and a potted plant.

18. 1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.4 out of 10, Very good, (28 reviews)
"Exactly as advertised, comfortable bed easy entry, overall great experience."
United States
Monte P.
The price is ￥18,337
￥30,979 total
includes taxes & fees
Nov 2 - Nov 3
1 bedroom 1 bath private entrance
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

19. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is ￥50,121
￥57,640 total
includes taxes & fees
Nov 4 - Nov 5
Guesthouse at Norwalk Inn
A spacious living area with a ping pong table, a covered sofa, and a dining table.

20. Charming 1-bedroom apartment in Dix Hills with AC, WiFi, fitness room, ping pong

Charming 1-bedroom apartment in Dix Hills with AC, WiFi, fitness room, ping pong
Dix Hills
The price is ￥25,554
￥35,468 total
includes taxes & fees
Oct 26 - Oct 27
Charming 1-bedroom apartment in Dix Hills with AC, WiFi, fitness room, ping pong
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

Viana Hotel and Spa, Trademark Collection by Wyndham

Viana Hotel and Spa, Trademark Collection by Wyndham

10/10 Excellent
"Bar staff (Dillon and Alejandra) are extremely friendly and professional. Ditto for the front desk staff."
J. Daniel 6-night trip
Posted less than an hour ago
Viana Hotel and Spa, Trademark Collection by Wyndham

Find out more about Smithtown

Search for holiday rentals in Smithtown on Expedia! You can easily find your home rentals, villas, holiday apartments in Smithtown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Smithtown!

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?

Large Beach House Steps From Town and Ocean: This vacation home rental outside of Smithtown has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 paces steakhouse 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.