Photo by Doug Kerr

Smithtown Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Smithtown

DUNE Fairfield Beach
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (41)
"The property is generally old, but it was a nice renovation. Of the room. "
The price is CA $418
CA $623 total
includes taxes & fees
Nov 22 - Nov 23
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
The President Mansion Luxurious 7BR Family Retreat
Interior
The President Mansion Luxurious 7BR Family Retreat
9.6 out of 10, Exceptional, (4)
"I booked this property for my in-laws to stay at for the weekend of my wedding. There was plenty of space for all the adults and the kids to stay comfortably. The host was helpful, attentive, and accommodating. I would happily stay here again in the future. "
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
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, (23)
"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
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, (18)
"Jennifer was a nice host, very communicative. We felt very at home and safe. There was no noise and it was peaceful, I would definitely book here again, thanks Jeniffier!!!"
The price is CA $134
CA $209 total
includes taxes & fees
Dec 9 - Dec 10
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
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
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils
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.
1 bedroom 1 bath private entrance
1 bedroom, WiFi, bed sheets
1 bedroom 1 bath private entrance
8.8 out of 10, Excellent, (15)
"Great place to stay for just needing a bed after a wedding. Owner very accommodating and friendly. "
The price is CA $183
CA $276 total
includes taxes & fees
Nov 18 - Nov 19
1 bedroom 1 bath private entrance
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
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, (73)
"Joe was an amazing and kind host. The house has the most unbelievably scenic backyard, with just incredible natural wild life. Was out of a movie. The house if very well equipped for everything you need and is in an amazing location - walk to beach or to town. Really, really an amazing stay. "
Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private
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 $318
CA $366 total
includes taxes & fees
Dec 8 - Dec 9
Guesthouse at Norwalk Inn
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 $200
CA $330 total
includes taxes & fees
Nov 18 - Nov 19
Private 1 bedroom apt in a quiet neighborhood, close to all!
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.
9.6 out of 10, Exceptional, (7)
"In town overnight for a funeral. The house was so close to family. Comfortable and clean"
The price is CA $422
CA $631 total
includes taxes & fees
Nov 18 - Nov 19
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Beach Apt. Wineries, Shopping, Dining
Property grounds
Beach Apt. Wineries, Shopping, Dining
5.2 out of 10, (7)
"Host was so helpful with check in! Place was super clean and conveniently located near town. Loved the place from top to bottom! 10/10 would recommend! "
The price is CA $176
CA $378 total
includes taxes & fees
Nov 22 - Nov 23
Beach Apt. Wineries, Shopping, Dining
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
On the beach
Soundview Beach House: 4BR,Panoramic Views 1.5hrsNYC, Sits Directly on beach
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 1.5hrsNYC, Sits Directly on beach
Waterfront Cottage cute and cozy
Interior
Waterfront Cottage cute and cozy
9.4 out of 10, Exceptional, (93)
"We loved the place, location & view. We will definitely be using this place again !!"
The price is CA $176
CA $360 total
includes taxes & fees
Nov 18 - Nov 19
Waterfront Cottage cute and cozy
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, (43)
"The place was great! The host though of everything, literally. Things that you wouldn't think would even be needed were there. Everything was excellent, cozy and very welcoming. The property was exactly as discribed. I can't say enough about the cleanliness and cozy vibe. We look forward to staying again if we are ever in the area. Ewarm and welcoming. "
Beautifully decorated1BR Apartment - Full Kitchen, Private Backyard & Fire Pit!
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.
Don't see what you're looking for?
See all available properties in Smithtown
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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, (1003)
"Great"
The price is CA $190
CA $217 total
includes taxes & fees
Nov 24 - Nov 25
Hyatt Regency 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, (1012)
"Excellent "
The price is CA $127
CA $142 total
includes taxes & fees
Dec 5 - Dec 6
Inn at Jericho
East Norwich Inn
Exterior
East Norwich Inn
2.5 star property
8.0 out of 10, Very good, (1755)
"Honestly, this place was exactly what I needed for an reasonably priced weekend stay. It wasn't the Ritz, but I didn't need or pay that. The property is dated, but so are most of the hotels in the area. It was clean, managed, and I had housekeeping services everyday. Next time I need a short or long visit, I'll definitely consider this property!"
The price is CA $132
CA $147 total
includes taxes & fees
Nov 25 - Nov 26
East Norwich Inn
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?

Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres : This vacation home rental outside of Smithtown is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease 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. 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.