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1 Aug - 3 Aug
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22 Aug - 24 Aug
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19 Sep - 21 Sep

Vacation Homes in Smithtown

Serene Beach Cottage Robbins Rest, Fire Island
Terrace/patio

Serene Beach Cottage Robbins Rest, Fire Island

Serene Beach Cottage Robbins Rest, Fire Island
Spacious 5-bedroom house in charming Bay Shore with AC, WiFi
Private kitchen

Spacious 5-bedroom house in charming Bay Shore with AC, WiFi

4.8 out of 10, (3)
"Lots of space, great location, suited our extended family well."
Spacious 5-bedroom house in charming Bay Shore with AC, WiFi
Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach
Fridge, microwave, stovetop, coffee/tea maker

Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

10.0 out of 10, Exceptional, (2)
"Everything was as pictured, and the whole place was very clean. It was a perfect stay for us, and we will come again soon!"
The price is SAR 500
SAR 871 total
includes taxes & fees
5 Aug - 6 Aug
Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville
Exterior

Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville

10.0 out of 10, Exceptional, (82)
"Great location. Very peaceful. Great house"
Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville
Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park
Beach

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park
Waterfront & private beach Scandinavian style house near Bellport, NY
Interior

Waterfront & private beach Scandinavian style house near Bellport, NY

9.6 out of 10, Exceptional, (54)
"Beautiful views and a comfortable stay."
Waterfront & private beach Scandinavian style house near Bellport, NY
Updated home in great location with spacious living & outdoor features
Property grounds

Updated home in great location with spacious living & outdoor features

8.8 out of 10, Excellent, (58)
"Bunk beds, it was very clean and kitchen was great"
Updated home in great location with spacious living & outdoor features
Charming 1-bedroom house in Ronkonkoma with AC, WiFi, Washer & Dryer
Microwave, oven, stovetop, dishwasher

Charming 1-bedroom house in Ronkonkoma with AC, WiFi, Washer & Dryer

9.0 out of 10, Wonderful, (4)
"Enjoyed our stay, property was as advertised. Quiet, comfortable neighborhood, and host was prompt with all communications."
The price is SAR 657
SAR 1,350 total
includes taxes & fees
8 Aug - 9 Aug
Charming 1-bedroom house in Ronkonkoma with AC, WiFi, Washer & Dryer
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Exterior

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (5)
"We had a very nice family weekend. There was plenty of room, the furniture and beds were comfortable, and the kitchen had everything we needed. Great communication with the owner"
The price is SAR 1,459
SAR 2,823 total
includes taxes & fees
27 Jul - 28 Jul
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
Outdoor dining

“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath

10.0 out of 10, Exceptional, (19)
"This is my second time staying here. Decorated beautifully, always clean and wonderful amenities. "
“The Cool House” Waterfront Oasis, 3 Bedrm 2 bath
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time
Property grounds

BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

10.0 out of 10, Exceptional, (10)
"Super enjoyable."
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time
Blue Cottage East Setauket
Fridge, microwave, oven, stovetop

Blue Cottage East Setauket

The price is SAR 934
SAR 2,539 total
includes taxes & fees
27 Jul - 28 Jul
Blue Cottage East Setauket
Beautiful historic home in Stony Brook!
Interior

Beautiful historic home in Stony Brook!

2.0 star property
8.0 out of 10, Very Good, (10)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!
Relaxing Smith Point Beach House on private canal
Outdoor dining

Relaxing Smith Point Beach House on private canal

9.6 out of 10, Exceptional, (58)
"Great location, so close to the beach! We very much enjoyed our time at the property, had everything we could need. The hosts were amazing!"
Relaxing Smith Point Beach House on private canal
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, (34)
"Great place. Total of 7 of us travelled. Will absolutely use this property again. Thank you for everything!"
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.
Kismet, Fire Island 4 bedroom family house "IMAGINE"
Property grounds

Kismet, Fire Island 4 bedroom family house "IMAGINE"

9.8 out of 10, Exceptional, (27)
"To quote my son, our stay at Imagine was a “top-tier week”! Everything was perfect and as described. We thoroughly enjoyed the incredible kitchen and outside deck. Fran was helpful and attentive, a wonderful host. Our family was happy and comfortable all week. Thank you to the Cintorino Family for sharing your home with our family 💙"
Kismet, Fire Island 4 bedroom family house "IMAGINE"
Courtland Haven
Living area

Courtland Haven

Courtland Haven
Lovely Basement with 2 Bedrooms and Kitchen
Fridge, microwave, oven, stovetop

Lovely Basement with 2 Bedrooms and Kitchen

10.0 out of 10, Exceptional, (15)
"We enjoyed our stay so much we’ve already booked a second stay!"
Lovely Basement with 2 Bedrooms and Kitchen
Bayfront Home in Patchogue w/ Deck & Fishing Dock
Fridge, microwave, stovetop, dishwasher

Bayfront Home in Patchogue w/ Deck & Fishing Dock

10.0 out of 10, Exceptional, (3)
"This is a beautiful property with tremendous views of the sunrise and the sunset have been enjoying our stay tremendously"
Bayfront Home in Patchogue w/ Deck & Fishing Dock
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, (25)
"Nice, private area. Perfect for a quick getaway."
Dog-friendly home just blocks from the bay with deck & private 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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Top Smithtown Hotel Reviews

The Circle Hotel Fairfield

The Circle Hotel Fairfield

10/10 Excellent
" Love staying here. Staff is friendly -courteous and professional. I am also happy that when possible they always have the room I love available. Thank you to everyone at the circle inn my stay is always the best."
Nancy 4-night trip
Posted 18 hours ago
The Circle Hotel Fairfield