Photo by Doug Kerr

Smithtown Vacation Rentals

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Check prices for these dates

Tonight
Apr 16 - Apr 17
Tomorrow
Apr 17 - Apr 18
This weekend
Apr 18 - Apr 20
Next weekend
Apr 25 - Apr 27

Vacation Rentals in Smithtown

DUNE Fairfield Beach
Private beach nearby, sun loungers, beach umbrellas, beach towels

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (52)
"All good"
The price is CA $309
CA $432 total
includes taxes & fees
Apr 17 - Apr 18
DUNE Fairfield Beach
Luxury and Affordable Family Home
Interior

Luxury and Affordable Family Home

10.0 out of 10, Exceptional, (2)
"My family and I had the pleasure of staying here during the Christmas holidays, and it was an excellent experience. We were especially grateful for the accessibility features, as my grandmother (85 years young), who uses a walker and had recently undergone surgery, was able to comfortably stay on the main floor. The property had just a few steps to enter, and best of all, there was a bedroom and full bathroom on the main level, along with ample room for a walker or wheelchair.The home itself was...
The price is CA $431
CA $1,061 total
includes taxes & fees
Apr 20 - Apr 21
Luxury and Affordable Family Home
fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc
Smart TV, books

fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

10.0 out of 10, Exceptional, (11)
"The property was as advertised. It was clean and there was plenty of room for my family of 4. The place is updated and has large tvs in each room. We all agreed that beds were awesome and made for a great nights sleep. The location was close to major highways, making it easy to get anywhere we needed to go. I would definitely stay here again. Thank you for a great stay!."
fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc
Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment
Exterior

Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment

10.0 out of 10, Exceptional, (16)
"We recently had the joy of staying here with family meeting from different parts of New York and New Jersey. House is beautiful, location is quiet and peaceful with a great view of the bay. Nearby to some great Long Island beaches. Loved the pool and amenities of the home. Faraz was an excellent host and extremely responsive to our needs "
The price is CA $1,214
CA $2,907 total
includes taxes & fees
Apr 21 - Apr 22
Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment
Waterfront Beach House 30 Min from New York City
Pool

Waterfront Beach House 30 Min from New York City

4.0 out of 10, (1)
"The house was clean, safe, and check-in process was smooth. Being on the water was nice to look at from afar. It served our purposes as we wanted to be near Jones Beach for a concert. However, several expectations were not met. This is listed as a "beach house" but there were no beach chairs or towels to bring to the beach. (Owner told us there would be via messaging.) The very first photo has a lovely lit-up porch, however the lights didn't work outside and we had to use our cell phones for...
Waterfront Beach House 30 Min from New York City
Guesthouse at Norwalk Inn
Studio Suite, Kitchen | Private kitchen

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"Great space would be better if there were kuerig cups to go with the machine in the kitchen"
The price is CA $388
CA $446 total
includes taxes & fees
May 12 - May 13
Guesthouse at Norwalk Inn
Beach Apt. Wineries, Shopping, Dining
Property grounds

Beach Apt. Wineries, Shopping, Dining

6.0 out of 10, (11)
"It was a decent place to stay."
The price is CA $132
CA $343 total
includes taxes & fees
Apr 19 - Apr 20
Beach Apt. Wineries, Shopping, Dining
1856 Trading House w/ walk to water
Smart TV, DVD player, books

1856 Trading House w/ walk to water

9.6 out of 10, Exceptional, (41)
"It was clean and just what we needed the calling fan didn't work but the AC did so no real deal breaker"
1856 Trading House w/ walk to water
The Raabbit Hole
Fridge, microwave, oven, stovetop

The Raabbit Hole

9.2 out of 10, Wonderful, (22)
"Only recommendation would be to upgrade the beach chairs . The house was very Homie and comfortable and plenty big. Would definitely stay again. "
The Raabbit Hole
Dog-friendly home just blocks from the bay with deck & private hot tub
TV

Dog-friendly home just blocks from the bay with deck & private hot tub

8.0 out of 10, Very good, (24)
"We loved the location, but the home was loaded with spiders, most appliances did not work (dishwasher did not work, blender, toaster oven, the stove top only half worked) - plus the pots were scratched (and with Teflon not useable) The shower door was broken and would not close, the toilet paper roll holder had no dowel to hold roll, toilet seat very loose, door frames were chipped and dirty, hold in wall next the bed in room with bunkbeds, laundry closet had missing doors. "
Dog-friendly home just blocks from the bay with deck & private hot tub
Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private
Exterior

Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private

10.0 out of 10, Exceptional, (76)
"Great location. Very peaceful. Great house"
Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private
3 Story Beach Waterview, 3 KING bed, golf putting green!
Aerial view

3 Story Beach Waterview, 3 KING bed, golf putting green!

10.0 out of 10, Exceptional, (15)
"We stayed on Long Island for 4 nights to coach a Perfect Game Baseball Tournament. This property was spacious enough to host my wife and I along with 4 other coaches (6 adults total). We were also able to bring our two jack russells with us. We had a great time, and look forward to staying here again."
The price is CA $208
CA $797 total
includes taxes & fees
Apr 22 - Apr 23
3 Story Beach Waterview, 3 KING bed, golf putting green!
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
Fridge, microwave, oven, stovetop

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

8.2 out of 10, Very good, (44)
"This house was very nice, as pictured or better. Clean, no issues checking in or out. Wagon was there as promised, more bikes than promised, lots of beach towels and chairs provided. The house had two wonderful outdoor second story decks with great views of the water and the ferry dock. Location was perfect, so convenient to ferry and market. Two things not great. Although it had an AC unit in every bedroom that all worked fine which made ground floor cool and comfortable, the main living...
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
Gatsby's - Heated Plunge Pool & Hot Tub in OBP, Sleeps 24, Steps From The Beach
Property grounds

Gatsby's - Heated Plunge Pool & Hot Tub in OBP, Sleeps 24, Steps From The Beach

Gatsby's - Heated Plunge Pool & Hot Tub in OBP, Sleeps 24, Steps From The Beach
Captain's Cottage - Cold Spring Harbor Water Views
Aerial view

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (58)
"Great place to stay in a cute community"
The price is CA $389
CA $792 total
includes taxes & fees
Apr 18 - Apr 19
Captain's Cottage - Cold Spring Harbor Water Views
Cheerful 4 bedrooms residential house.
Fridge, microwave, dishwasher, coffee/tea maker

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (30)
"Toocold in Connecticut, host was alway inclose contact, heat was our only issue "
Cheerful 4 bedrooms residential house.
Beautiful Private Studio Apartment!
Outdoor dining

Beautiful Private Studio Apartment!

9.6 out of 10, Exceptional, (5)
"we enjoyed our stay."
Beautiful Private Studio Apartment!
Cozy 1-bedroom apartment with WiFi, AC in peaceful North Babylon
1 bedroom, WiFi

Cozy 1-bedroom apartment with WiFi, AC in peaceful North Babylon

The price is CA $157
CA $330 total
includes taxes & fees
Apr 17 - Apr 18
Cozy 1-bedroom apartment with WiFi, AC in peaceful North Babylon
2 bedroom apartment minutes away from Gambling, Bars, Restaurants, Water Park...
Fridge, microwave, stovetop, coffee/tea maker

2 bedroom apartment minutes away from Gambling, Bars, Restaurants, Water Park...

8.4 out of 10, Very good, (9)
"If your looking for a place to get away from everyday life and just relax. This is your place. I would definitely come back again."
2 bedroom apartment minutes away from Gambling, Bars, Restaurants, Water Park...
1 bed room basement apartment.
Private kitchen

1 bed room basement apartment.

8.6 out of 10, Excellent, (8)
"The property was very spacious and can bring family there. "
The price is CA $139
CA $233 total
includes taxes & fees
Apr 19 - Apr 20
1 bed room basement apartment.
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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Other types of properties in Smithtown you may be interested in

Hampton Inn Long Island-Brookhaven
Gazebo

Hampton Inn Long Island-Brookhaven

2.5 star property
8.8 out of 10, Excellent, (1051)
"Nice place"
The price is CA $143
CA $164 total
includes taxes & fees
Apr 22 - Apr 23
Hampton Inn Long Island-Brookhaven
Hyatt Regency Long Island
Exterior

Hyatt Regency Long Island

3.5 star property
8.2 out of 10, Very good, (1005)
"The showers take a while to get warm. Never got very hot. Also, the shower head made the shower feel more like a beach rinse off than an actual shower. Other than that this was a very nice hotel. "
The price is CA $177
CA $202 total
includes taxes & fees
Apr 20 - Apr 21
Hyatt Regency Long Island
Viana Hotel and Spa, Trademark Collection by Wyndham
Exterior

Viana Hotel and Spa, Trademark Collection by Wyndham

4.0 star property
8.4 out of 10, Very good, (1002)
"It's old "
The price is CA $215
CA $240 total
includes taxes & fees
Apr 27 - Apr 28
Viana Hotel and Spa, Trademark Collection by Wyndham
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.

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?

Luxury and Affordable Family Home: This vacation home rental outside of Smithtown offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.