Photo by Doug Kerr

Smithtown Vacation Rentals

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Check prices for these dates

Tonight
Jan 18 - Jan 19
Tomorrow
Jan 19 - Jan 20
Next weekend
Jan 24 - Jan 26
In two weeks
Jan 31 - Feb 2

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, (46)
"Sweet location and they remodeled it nice. However, be warned the bar next door does loud live music and the whole building shakes. Would only reccomend to the young party crowd. Not ideal for families. The manager was nice and did try to offer a refund for a night. Not sure how many people want to hear music vibrating until 2am. Young me would not have cared. Sweet beach access"
The price is CA $309
CA $502 total
includes taxes & fees
Jan 31 - Feb 1
DUNE Fairfield Beach
Beachfront Romance: Rustic Home w/ Private Beach
On the beach

Beachfront Romance: Rustic Home w/ Private Beach

9.2 out of 10, Wonderful, (46)
"We were looking for a small and private beach house getaway for the weekend and found this hidden gem. Our property manager, Debbie, made herself available throughout our stay to answer all of our questions. Everything needed for our comfort weekend was provided. We strongly recommend this place for those who are looking to get away from the hustle and bustle of city life. We will be returning! "
Beachfront Romance: Rustic Home w/ Private Beach
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Private kitchen

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

10.0 out of 10, Exceptional, (25)
"stayed here with my parents and 4 other adults to visit my son at stony brook. The house is very clean and well decorated, new kitchen with all the necessary tools. We will stay here again. "
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
The President Mansion Luxurious 7BR Family Retreat
Interior

The President Mansion Luxurious 7BR Family Retreat

9.6 out of 10, Exceptional, (5)
"Large enough to sleep 12 adults and 8 children without difficulty! The game room for kids is fabulous and the master bath was a dream come true! Will stay again when visiting Long Island. May plan a summer beach week since so close to Beaches on the South Shore."
The President Mansion Luxurious 7BR Family Retreat
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
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 $398
CA $458 total
includes taxes & fees
Feb 3 - Feb 4
Guesthouse at Norwalk Inn
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
Outdoor pool

20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

8.8 out of 10, Excellent, (9)
"Clean, spacious home with an amazing pool in a quiet neighborhood. If you're looking for a quiet getaway a good choice!"
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Fridge, microwave, oven, stovetop

Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

9.4 out of 10, Exceptional, (8)
"Space was nice. Need top sheets on beds. Noisy location and basement tenant."
The price is CA $432
CA $642 total
includes taxes & fees
Jan 19 - Jan 20
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
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
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly
Interior

Charming home close to beach with fast WiFi & washer/dryer - dog-friendly

7.6 out of 10, Good, (9)
"It was as cute as it looked on-line and gave us a great space for hanging out and enjoying each other's company. That said, I would recommend that you rent this with loved ones as privacy is limited because of the indoor design. With no insulation or dry wall every noise is heard throughout the house! Other nice surprises: new AC units (very quiet), very comfortable beds, and an outdoor shower with good light. The street is very quiet. I was surprised that basic kitchen supplies weren't included...
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bedroom, iron/ironing board, WiFi, bed sheets

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

9.4 out of 10, Exceptional, (20)
"I really enjoyed my stay. It was convenient and exceeded my expectations. When I am in town again I will definitely book again."
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bedroom 1 bath private entrance
1 bedroom, WiFi, bed sheets

1 bedroom 1 bath private entrance

9.0 out of 10, Wonderful, (17)
"Augustine was very helpful and nice!It was a great price that enabled us to visit friends and family for the holidays "
The price is CA $187
CA $287 total
includes taxes & fees
Jan 21 - Jan 22
1 bedroom 1 bath private entrance
Private 1 bedroom apt in a quiet neighborhood, close to all!
Fridge, microwave, oven, stovetop

Private 1 bedroom apt in a quiet neighborhood, close to all!

9.6 out of 10, Exceptional, (20)
"This apartment was perfect for me. I was in town for a Stony Brook parents weekend and was in close proximity to everything I needed. Comfy bed, very clean, private, and I liked having my coffee out on my patio in the mornings. Great communication from the owner as well. A+ all around!"
The price is CA $204
CA $347 total
includes taxes & fees
Jan 19 - Jan 20
Private 1 bedroom apt in a quiet neighborhood, close to all!
Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome
TV, fireplace

Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome

6.2 out of 10, (14)
"We all had an amazing time. Convenience to the beach was a bonus. Spectacular views of the ocean n the bay. Plenty of space , screen doors were annoying ( but I also live on the beach and understand how beat up everything gets). Would definitely rent this house again."
Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome
Designer beach cottage & studio with bikes, outdoor shower, deck - walk to beach
Fridge, microwave, oven, stovetop

Designer beach cottage & studio with bikes, outdoor shower, deck - walk to beach

9.2 out of 10, Wonderful, (20)
"Stayed here for a girls trip. We were a group of 11. Most of the beds are doubles so probably can’t actually sleep 12 unless you’re a kid or on the smaller side. The way the beds are arranged requires one person to crawl over the other to get out of bed since they’re pushed up against the wall. (Not a dealbreaker but something to consider for guest comfort). As others have mentioned, feels bigger than it looks in the photos. The bathrooms were ok. To break it down: there’s 1 half bath...
Designer beach cottage & studio with bikes, outdoor shower, deck - walk to beach
2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment
Fridge, microwave, oven, stovetop

2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment

8.8 out of 10, Excellent, (26)
"This property is steps away from the ferry, steps away from the beach and steps away from food, drinks and music. We had a great time. Cassie greeted us and made sure we had everything we needed!!!! She also went out of her way to make my daughters 21st birthday special. Highly recommend this property."
2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment
Beautifully decorated1BR Apartment - Full Kitchen, Private Backyard & Fire Pit!
Terrace/patio

Beautifully decorated1BR Apartment - Full Kitchen, Private Backyard & Fire Pit!

10.0 out of 10, Exceptional, (44)
"Just what we needed for a few days on Long Island Close to everywhere we needed to be Scott was always quick to respond! "
Beautifully decorated1BR Apartment - Full Kitchen, Private Backyard & Fire Pit!
Studio OSM · Sunny Westport Studio Apt. Above Historic Mill
Dining

Studio OSM · Sunny Westport Studio Apt. Above Historic Mill

10.0 out of 10, Exceptional, (68)
"We arrived later than the posted check in and Gerard and we spoke on the phone and everything went well. We felt like we were home. The apartment is all that it said in the ad were very accurate. Quaint, cozy and no hotel hassle. The next time we visit we will definitely look for this place!"
Studio OSM · Sunny Westport Studio Apt. Above Historic Mill
Soundview Beach House: 4BR, Panoramic Views
Outdoor dining

Soundview Beach House: 4BR, Panoramic Views

9.8 out of 10, Exceptional, (64)
"The house was exactly as advertised, the water views were beautiful! Easy access to the North Fork of Long Island."
Soundview Beach House: 4BR, Panoramic Views
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Fridge, microwave, oven, stovetop

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
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

Hyatt Regency Long Island
Exterior

Hyatt Regency Long Island

3.5 star property
8.2 out of 10, Very good, (1005)
"Let me start by saying the front desk, Elizabeth was absolutely fantastic! She went out her way for anything that we needed for the wedding , I was attending . I can not express my gratitude towards her . She made our stay so incredibly special and making us feel so welcomed. She deserves to be celebrated for all she does . I watched her with other guest and she treated each one with respect and kindness that she had expressed . I again would like to say Thank you to her she was off the day we...
The price is CA $160
CA $182 total
includes taxes & fees
Jan 26 - Jan 27
Hyatt Regency Long Island
Radisson Hotel Hauppauge-Long Island
Breakfast served, American cuisine

Radisson Hotel Hauppauge-Long Island

3.5 star property
6.0 out of 10, (1005)
"Overall good "
The price is CA $176
CA $201 total
includes taxes & fees
Jan 21 - Jan 22
Radisson Hotel Hauppauge-Long Island
Inn at Jericho
Standard Room, 1 Queen Bed, Accessible

Inn at Jericho

2.0 star property
8.0 out of 10, Very good, (1006)
"Loved it"
The price is CA $101
CA $113 total
includes taxes & fees
Feb 6 - Feb 7
Inn at Jericho
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?

Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.: This vacation home rental outside of Smithtown offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

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.