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Vacation Homes in Smithtown

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

9.2 out of 10, Wonderful, (22)
"its small but very nice for a short stay would recommend."
$144 nightly
The price is $165
Aug 10 - Aug 11
Total includes taxes and fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (65)
"Very nice place for a family to stay"
$1,219 nightly
The price is $1,393
Sep 1 - Sep 2
Total includes taxes and fees
Newly Renovated Luxury Beach House Ocean Bay Park

Waterfront Beach House 30 Min from New York City

6.8 out of 10, (6)
"The place was adorable and clean but had a very musty smell and tons of tiny ants, even in bathroom. The flooring was separting, probably from poor installation. "
Waterfront Beach House 30 Min from New York City

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (65)
"Great home to stay. Beautiful area to explore!"
$711 nightly
The price is $812
Sep 8 - Sep 9
Total includes taxes and fees
Captain's Cottage - Cold Spring Harbor Water Views

Stareway to Heaven Su

10.0 out of 10, Exceptional, (6)
Stareway to Heaven Su

Walkable to all in Downtown Seaford! Clean 1 bed basement unit

9.8 out of 10, Exceptional, (9)
"We were so happy to find this little gem in Seaford! Perfect location and perfect little home away from home. It has everything you need and easy access to everything nearby. We look forward to staying there again when we visit LI!"
Walkable to all in Downtown Seaford! Clean 1 bed basement unit

Charming 3-bedroom modern family retreat!

10.0 out of 10, Exceptional, (1)
"Spacious, clean and host was very responsive to any questions we had ! "
$407 nightly
The price is $465
Sep 2 - Sep 3
Total includes taxes and fees
Charming 3-bedroom modern family retreat!

Beautiful historic home in Stony Brook!

2.0 star property
8.2 out of 10, Very Good, (12)
"Thank you Great Location Would book again"
Beautiful historic home in Stony Brook!

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!"
$147 nightly
The price is $167
Aug 17 - Aug 18
Total includes taxes and fees
Charming 1-bedroom apartment-20 minutes from the Hamptons! 10 minutes from beach

Amazing Rocky Point Retreat Overlooking the Sound!

9.8 out of 10, Exceptional, (73)
"Love staying at this comfortable house each year for Thanksgiving and the location is perfect! "
Amazing Rocky Point Retreat Overlooking the Sound!

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

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

9.8 out of 10, Exceptional, (63)
"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

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.

Tranquil & Pet-Friendly Estate on Long Island!

10.0 out of 10, Exceptional, (6)
"We had a very enjoyable stay. The house was stocked with everything you would need.It was clean and neat.This house has lot of character. Idefinitely stay here again "
Tranquil & Pet-Friendly Estate on Long Island!

Charming New York Escape Near Central Park!

7.2 out of 10, Good, (15)
"This property was as described in the listing and though definitely not the newest house around, it definitely shows that efforts have been made to make it very hospitable for the modern traveler. The wifi speed was even better than what my geeky husband has at home & the kitchen had all the modern conveniences. Though a little tight, the upstairs bathroom has beautiful accents that elevate the space. There are artistic style choices throughout that made the property feel like a stylish home...
Charming New York Escape Near Central Park!

Stay at Black Rock Harbor

10.0 out of 10, Exceptional, (21)
"Lovely home, responsive host & convenient location with water views. Cute & comfy decor with well appointed kitchen and off street parking. "
Stay at Black Rock Harbor

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"
$614 nightly
The price is $697
Sep 3 - Sep 4
Total includes taxes and fees
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

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

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

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

$302 nightly
The price is $344
Aug 13 - Aug 14
Total includes taxes and fees
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic 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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Top Smithtown Hotel Reviews