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Compare 385 Vacation Homes in Smithtown with updated reviews, rates, and availability.

Fully Renovated 4 bedroom 2 bath home in the heart of Ocean Beach

9.8 out of 10, Exceptional, (8)
"Matthew was so helpful leading up to our stay. He walked us through the check-in process clearly and answered any and all questions about our stay. Thank you!"
Fully Renovated 4 bedroom 2 bath home in the heart of Ocean Beach

Cozy 3BR Near Huntington's Nightlife & Beach

2.0 star property
6.0 out of 10, (2)
"Situated just off the main street of Huntington, this comfy cottage is a terrific home base for exploring the north shore area. It has ample space: generous sitting room and kitchen with modern amenities, private office area, and 3 large bedrooms with lots of closet space. The beds are perfectly firm, pillows are plump and sheets are oh-so soft. The bathroom has some updates and delivers the basics such as nice shower pressure and new sink/vanity. Very clean and tidy, parts of the home still...
Cozy 3BR Near Huntington's Nightlife & Beach

3BR Paradise in Port Jefferson!

3BR Paradise in Port Jefferson!

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.

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

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (25)
"Great communication and accommodations from the host. We were in town for a concert and the location couldn't have been better! Would recommend this stay for anyone looking within the area."
Cheerful 4 bedrooms residential house.

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

10.0 out of 10, Exceptional, (23)
"Overall, this was a great stay. The house was clean and as advertised. The location was perfect for us as we were visiting family in Lake Grove, Stonybrook, and Port Jeff. A few recommendations for minor improvements: more towel bars/hooks in the bathroom and an upgraded coffee maker. Regardless, we would happily stay here again when visiting Long Island. "
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (62)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Beautiful Beach House with Large Swimming Pool in Ocean Beach

10.0 out of 10, Exceptional, (34)
"Wonderful vacation! House has everything you need and the location is perfect. Hosts are quick to respond to any questions. Would definitely stay here again!"
Beautiful Beach House with Large Swimming Pool in Ocean Beach

Waterview House Walking Distance from Cove Beach

8.8 out of 10, Excellent, (15)
"We enjoyed the property very much. The view of the water was beautiful! The foos ball sets and pool tables were great additions and kept the kids (and adults😉) happily occupied. The third floor also provided a great place for the kids to “hang out”. Having a TV in each bedroom and the living room was nice. We needed a few things like additional hangers and dish towels and Elena was great about providing new ones very promptly! The kitchen accommodated our cooking needs well. Beds were...
The price is SAR 1,338
SAR 3,058 total
includes taxes & fees
23 Dec - 24 Dec
Waterview House Walking Distance from Cove Beach

Luxury and Affordable Family Home

The price is SAR 1,315
SAR 2,500 total
includes taxes & fees
19 Dec - 20 Dec
Luxury and Affordable Family Home

Marina Beach House - Pet Friendly

9.4 out of 10, Exceptional, (8)
"Super clean and beautifully decorated- would def book again. Host was very responsive to all questions. Gorgeous location as well! "
The price is SAR 1,785
SAR 2,683 total
includes taxes & fees
19 Dec - 20 Dec
Marina Beach House - Pet Friendly

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

9.4 out of 10, Exceptional, (19)
"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.

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

10.0 out of 10, Exceptional, (74)
"What a great home base for my family during Thanksgiving week! This house is everything it says it is and more. I seriously felt like I was a guest visiting family for the week. Too many awesome accommodations to list. The view out of the back windows, the bright coastal vibe, the home/audio setup, the huge/clean hot tub, the insanely awesome master bathrom!! What a neat house! Thanks, Joe for making our trip to the area a memorable one!"
Sayville Area-Exquisite Beachhouse, Stunning, Picturesque, Huge Hot Tub, Private

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 SAR 1,127
SAR 1,698 total
includes taxes & fees
19 Dec - 20 Dec
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

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

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (52)
"The captain cottage was exactly what Mom and I wanted! Beautiful views of the bay,super easy five minute walk to the main street of Cold Spring Harbor, adorable house with everything you need, and Kim was on top of it every time we neededhelp. Thank you so much for hosting us and cannot wait to be back!"
The price is SAR 909
SAR 1,771 total
includes taxes & fees
15 Jan - 16 January 2025
Captain's Cottage - Cold Spring Harbor Water Views

Waterfront Sunset Oasis Beach House Village Brewery Winery East End NYC 1 Hr

10.0 out of 10, Exceptional, (4)
"Perfect location to enjoy Northport! Everything is within walking distance. Host was very helpful and accommodating. Great stay and will definitely return! "
Waterfront Sunset Oasis Beach House Village Brewery Winery East End NYC 1 Hr

Charming New York Escape Near Central Park!

7.0 out of 10, Good, (6)
"Got dropped off at the H-Mart from the airport and did my shopping and then walked over, as the host mentioned it was within walking distance and they were right! Super convenient. Well laid out, thoughtful instructions, everything was super easy. Ideal location for a couple of adults to stay to attend a convention. Also, there are workspaces in both of the bedrooms, which was a nice touch. "
Charming New York Escape Near Central Park!

Stylish Sunset Retreat: Near Beach, Pool, Hot Tub

9.4 out of 10, Exceptional, (17)
"Overall 👍👍👍👍 Perfect area and vicinity to our wedding venue very nice neighborhood house was perfect unfortunately had to leave a day early due to New York City Marathon. ** Will definitely try to rent in the summer months"
Stylish Sunset Retreat: Near Beach, Pool, Hot Tub
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 property types in Smithtown

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (43)
"The property is generally old, but it was a nice renovation. Of the room. "
The price is SAR 1,066
SAR 1,606 total
includes taxes & fees
27 Dec - 28 Dec
DUNE Fairfield 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

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
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.