Photo by Doug Kerr

Search Cottages in Smithtown

    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

Compare 38 Cottages in Smithtown with updated reviews, rates, and availability.

Waterfront Cottage cute and cozy
Outdoor dining
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 AED 459
AED 940 total
includes taxes & fees
18 Nov - 19 Nov
Waterfront Cottage cute and cozy
Wow Seaside Beach Cottage Sunset Oasis Walk Waterfront Village East End NYC 1 Hr
Miscellaneous
Wow Seaside Beach Cottage Sunset Oasis Walk Waterfront Village East End NYC 1 Hr
8.4 out of 10, Very Good, (5)
"I enjoyed my stay here. The cottage was snug but clean. My host was friendly and helpful. ( Actually gave me a pound of really good coffee) Northport is a very pretty village with lots of interesting shops and art galleries as well as a Playhouse with surprisingly excellent talent. "
The price is AED 624
AED 915 total
includes taxes & fees
26 Nov - 27 Nov
Wow Seaside Beach Cottage Sunset Oasis Walk Waterfront Village East End NYC 1 Hr
Beach house cottage steps to private beach in the heart of Bayville
Beach
Beach house cottage steps to private beach in the heart of Bayville
10.0 out of 10, Exceptional, (9)
"Great location. Very clean modern cottage by the sea. Would love to stay again. "
Beach house cottage steps to private beach in the heart of Bayville
Cozy Riverside Cottage
Exterior
Cozy Riverside Cottage
10.0 out of 10, Exceptional, (1)
"Cottage is very comfortable and clean. Neighborhood is quiet and in natural surroundings. Be prepared for spotty reception (screenshot access code) but WiFi is excellent in home, so is the TV/music system. Over all, excellent value and great accommodations in a beautiful spot. Only needed it for the weekend, but would book as a destination for some peace and quiet."
Cozy Riverside Cottage
Cozy Country Cottage #4
Property grounds
Cozy Country Cottage #4
10.0 out of 10, Exceptional, (3)
"Rob was great. The neighborhood was great. The house was great. If you are a baseball player, you'll love this place! Will return."
Cozy Country Cottage #4
Charming Patchogue Cottage!!!
Living area
Charming Patchogue Cottage!!!
10.0 out of 10, Exceptional, (5)
"Loved it. Had everything we needed for a short stay to visit family. Perfect location, beautiful decor and all the necessities plus more! Thank you Brianna and Stephen for a wonderful stay…"
Charming Patchogue Cottage!!!
Fairfield Cottage · Charming Fairfield Cottage By The Sea
Fairfield Cottage · Charming Fairfield Cottage By The Sea
10.0 out of 10, Exceptional, (31)
"What a wonderful find, and only an hour away from NYC. Fairfield CT is beautiful, friendly people, great restaurants, dog friendly, beautiful private beach, the list goes on and on. Thank you to Gerard for being so helpful, kind and always there to answer any questions, and give great recommendations. If you ever need a break from the city, this is the place to go to. Thanks again for such a wonderful holiday! We will be back."
Fairfield Cottage · Charming Fairfield Cottage By The Sea
Beachfront Romance: Rustic Home w/ Private Beach
A cozy home by the sea!
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
Westport "Gold Coast" across from Southport beach
Property grounds
Westport "Gold Coast" across from Southport beach
10.0 out of 10, Exceptional, (82)
"Had the best time. Walked to the beach. Great local restaurants as well."
Westport "Gold Coast" across from Southport beach
Designer cottage with amazing view, serene deck & outdoor shower - walk to beach
Designer cottage with amazing view, serene deck & outdoor shower - walk to beach
9.6 out of 10, Exceptional, (21)
"We absolutely loved our stay at huron hideaway! The house was spotless upon our arrival, the decor was beautiful and we felt relaxed and right at home the minute we stepped in. The proximity to the beach was perfect!! We absolutely will be back!!"
Designer cottage with amazing view, serene deck & outdoor shower - walk to beach
Bay Shore Vacation Rental ~ 7 Mi to the Beach
Living area
Bay Shore Vacation Rental ~ 7 Mi to the Beach
3.0 star property
10.0 out of 10, Exceptional, (1)
Bay Shore Vacation Rental ~ 7 Mi to the Beach
Second floor cottage apartment located in a private community.
Living Room with view towards Bedroom 1
Second floor cottage apartment located in a private community.
9.6 out of 10, Exceptional, (14)
"What a lovely apartment hidden away on a private street. It is very clean and well-kept, and extra attention is given to making sure guests have what they need. Communication with hosts was easy and straightforward. We were very pleased with our stay. "
Second floor cottage apartment located in a private community.
Cozy Country Cottage #2
entrance to cottage number 2
Cozy Country Cottage #2
7.4 out of 10, Good, (6)
"I booked this property as I was running my first 50-mile race and it was located within 2 miles from the starting trailhead! I wanted a place close by that was big enough to house 4 people total and this cottage provided exactly that. The pictures don’t do it justice truthfully as it was much bigger than I thought it was going to be. The house was very cozy and welcoming, and provided everything I needed for a weekend away. I will definitely book it again! "
The price is AED 588
AED 1,080 total
includes taxes & fees
16 Nov - 17 Nov
Cozy Country Cottage #2
Beachfront cottage located in the heart of Fairfield Beach!!
Outdoor dining
Beachfront cottage located in the heart of Fairfield Beach!!
9.6 out of 10, Exceptional, (15)
"This is my third year staying at this property. I have friends that live around the area so it is a nice quiet private space to reconnect. Paul the host is always quick to respond to any concerns I may have while staying. My dog Angel is in heaven literally 5 steps to the water . The beach and people are so kind and friendly. Love it!"
Beachfront cottage located in the heart of Fairfield Beach!!
Luxury Beach Cottage: Wineries, Shopping & The Hamptons
Outdoor seats and grill at the patio
Luxury Beach Cottage: Wineries, Shopping & The Hamptons
10.0 out of 10, Exceptional, (25)
"A wonderful home, incredible location, views breathtaking"
Luxury Beach Cottage: Wineries, Shopping & The Hamptons
Charming New York Escape Near Central Park!
Private kitchen
Charming New York Escape Near Central Park!
3.0 star property
Charming New York Escape Near Central Park!
Sun and Fun on the beach!!
You are here!
Sun and Fun on the beach!!
9.6 out of 10, Exceptional, (15)
"Very good place on the beach….and beach walking Paul communication was very timely"
Sun and Fun on the beach!!
Long Island Home Near Beaches & Golf
Exterior
Long Island Home Near Beaches & Golf
3.0 star property
Long Island Home Near Beaches & Golf
North Babylon Home, Near Belmont Lake State Park!
Exterior
North Babylon Home, Near Belmont Lake State Park!
3.0 star property
North Babylon Home, Near Belmont Lake State Park!
Charming Rocky Point Home ~ 1 Mi to Beach!
Exterior
Charming Rocky Point Home ~ 1 Mi to Beach!
3.0 star property
Charming Rocky Point Home ~ 1 Mi to Beach!
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 property types in Smithtown

DUNE Fairfield Beach
Room
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 AED 937
AED 1,416 total
includes taxes & fees
21 Nov - 22 Nov
DUNE Fairfield Beach
Beachfront Romance: Rustic Home w/ Private Beach
A cozy home by the sea!
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
Exterior
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
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

Why book your cottage in Smithtown with Expedia?
Expedia has some superb cottages in Smithtown, so get set for an unforgettable stay on nature’s doorstep. If you need to stick to a budget, choose how much you’re willing to spend and the star rating of your property. Or, make your way to the filters to search for cottages with a kitchen or a pool. We’ll help you find a suitable place whatever your plans or style of travel.
How can I find cheap cottages in Smithtown?
Expedia can help you easily locate cheap cottages in Smithtown. To book your dream stay in a few quick clicks, use the filter tool to refine your search results by amenities, star rating and budget.