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Compare 339 Vacation Homes in Smithtown with updated reviews, rates, and availability.

Waterfront Home magnificent view!
9.4 out of 10, Exceptional, (90)
"It was a nice fun relaxing weekend for my lady and I here at Michael’s property. We really enjoyed :) our second time here!"
The price is AED 459
AED 926 total
includes taxes & fees
21 May - 22 May
Waterfront Home magnificent view!
Room
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
9.6 out of 10, Exceptional, (8)
"Nice place to stay. Small but has everything you need. Close to the major highways. Hostess Jennifer was great She checked in several times with me."
The price is AED 349
AED 544 total
includes taxes & fees
21 May - 22 May
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Room
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
10.0 out of 10, Exceptional, (1)
"Kerry was a great host! The home was new, clean, modern, and beautifully decorated. The home and host exceeded our expectations. Kerry was friendly, available and very communicative. We’ll book again."
The price is AED 1,469
AED 2,729 total
includes taxes & fees
20 May - 21 May
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
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Exterior
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
9.4 out of 10, Exceptional, (11)
"The house and property were very nice but we expected there to be more beds"
The price is AED 2,938
AED 3,776 total
includes taxes & fees
19 May - 20 May
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
Brand New Rebuild - Stunning Luxury on the Beach!
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters
10.0 out of 10, Exceptional, (49)
"Beautiful home in a great location with a wonderful view. Thoughtfully designed, furnished and stocked with everything you'll need. Also, great communication from the owners! Spent the weekend with teens and can't wait to return for a more relaxing adult trip!"
Windows on the Sea ★ Modern Pool & Beach Retreat ★ 100 ft to Beach ★ 2 Masters
Exterior
Beautiful 3 Bedroom house
10.0 out of 10, Exceptional, (2)
"This was an amazing house with an amazing host!! I spent 5 days this month and loved everything about my stay. The owner is extremely kind and accommodating! If you need a home away from home or a staycation on Long Island, this beautiful 3 br and GORGEOUS yard! 5stars😊"
Beautiful 3 Bedroom house
Living area
Bellport Luxury Pool Retreat w/ 3BR
The price is AED 1,365
AED 2,099 total
includes taxes & fees
19 May - 20 May
Bellport Luxury Pool Retreat w/ 3BR
Exterior
Stunning 7-bedroom 8000 SQFT Mansion with 3 car garage in Bayshore New York
Stunning 7-bedroom 8000 SQFT Mansion with 3 car garage in Bayshore New York
Ample seating, perfect for lounging, gathering, and yes, napping.
Peaceful home-away-from-home centrally located in the heart of Long Island.
10.0 out of 10, Exceptional, (1)
"Cool house, plenty of room, great location near Village"
Peaceful home-away-from-home centrally located in the heart of Long Island.
🌟Sunlit room with a cozy queen bed & chic work nook. #HomeOffice #SleepInStyle
💎 Modern Chic Getaway, Biz Friendly, Close 2 all 👣
💎 Modern Chic Getaway, Biz Friendly, Close 2 all 👣
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly
8.4 out of 10, Very Good, (5)
"We found the house to be really cute and fun to stay in. The location was excellent and we even saw a deer on our last morning! Our main issues, and why this isn’t a 5 star rating, were that multiple lighting fixtures weren’t working and there was an entire bed missing. The ad mentions “1 queen, 1 double, 4 twin’ beds however there’s really 1 queen and 4 twins. This could have caused a big problem if our group was just a bit larger. The ad should be changed to reflect the accurate information...
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly
Living area
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
The price is AED 790
AED 1,297 total
includes taxes & fees
19 May - 20 May
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Living area
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
10.0 out of 10, Exceptional, (7)
"The house was amazing, the location was perfect I could see the ocean from the living room. The only issues were the flooded roads and a few lights with dead bulbs but the flooding is understandable since its so close to the ocean. Overall we had a great time and would definitely come back."
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
Farmingdale Vacation Rental | 2BR | 1BA | 1,100 Sq Ft | Step-Free Entry
Long Island Home w/ Deck, Yard, 5 Mi to Beach!
6.8 out of 10, (5)
"House was very nice and clean definitely stay again"
Long Island Home w/ Deck, Yard, 5 Mi to Beach!
Interior
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
10.0 out of 10, Exceptional, (12)
"Stayed at Coastal Retreat for a weekend visit with son who attends Fairfield University, brought both sets of parents and teen daughter (ages ranging 73-16), plenty of room and able to enjoy a wonderful family dinner with son even in attendance. Wonderful area, close walk to beach and easy to get to downtown Fairfield and university. Very clean and welcoming! Greg was wonderful to work with and answered any question we had that came up both prior and upon arrival. The only thing we would mention...
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Exterior
Cheerful 4 bedrooms residential house.
9.8 out of 10, Exceptional, (13)
"This was walking distance to the Total Mortgage Arena for our robotics competition. Having the full kitchen to cook meals was awesome. Nice comfy beds, plenty of space, I claimed the nook off the kitchen/dining area for myself. Boys had front room to work on their robot."
Cheerful 4 bedrooms residential house.
Living area
Beautiful 3 BR Full House w/ King Bed on Dead End- 5 min from town!
9.8 out of 10, Exceptional, (11)
"Great location to visit family on the South Shore. Easy access to town/restaurants. Very responsive host! We’ll be back."
Beautiful 3 BR Full House w/ King Bed on Dead End- 5 min from town!
Updated home in great location with spacious living & outdoor features
8.8 out of 10, Excellent, (49)
"We got to the house and it was a lovely house, in a great location. The garbage outside had meat and other garbage not in bags. The storm door was broken which we fixed ourselves, the floor was full of sand, the air conditioner in the kitchen didnt blow cold air and the fan in the ktchen didnt work either, the remote was nowhere to be found. I think some of our money should be refunded."
Updated home in great location with spacious living & outdoor features
Spacious Home Located Close to Stony Brook!
9.0 out of 10, Wonderful, (2)
"It was a good place for what we needed. Only issues were a very loose handrail to the second floor and the wall ways were not shoveled and were slippery"
The price is AED 1,466
AED 2,769 total
includes taxes & fees
19 May - 20 May
Spacious Home Located Close to Stony Brook!
Relax with a local wine and cheese on your deck watching the beautiful sunset!
Luxurious Waterfront Beach House On The Bay
9.8 out of 10, Exceptional, (30)
"The location is quiet and beautiful. Steve and Dory are darlings and really know how to welcome guests. Everything was perfect and easy. They even had us set up with a rental bike company. We would stay again in a heartbeat."
Luxurious Waterfront Beach House On The Bay
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See all available properties in Smithtown
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.

Other property types in Smithtown

Room
DUNE Fairfield Beach
3.0 star property
10.0 out of 10, Exceptional, (10)
"Modern cottage near the beach. Clean and comfortable. Very responsive."
The price is AED 779
AED 1,071 total
includes taxes & fees
20 May - 21 May
DUNE Fairfield Beach
Exterior
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
9.4 out of 10, Exceptional, (11)
"The house and property were very nice but we expected there to be more beds"
The price is AED 2,938
AED 3,776 total
includes taxes & fees
19 May - 20 May
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
A cozy home by the sea!
Beachfront Romance: Rustic Home w/ Private Beach
9.2 out of 10, Wonderful, (39)
"The house is small but it has everything you need. The ocean was lovely to watch and good scavenging for rocks and sea glass. Very private place. My pup and I had a good time!"
Beachfront Romance: Rustic Home w/ Private 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.

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