Holiday Homes in Smithtown

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Our top choices for Smithtown holiday homes

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (75 reviews)
"Location was perfect!"
United States
Linda J P.
The price is AU$658
includes taxes & fees
20 Apr - 21 Apr
Captain's Cottage - Cold Spring Harbor Water Views

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
Spacious 3BR Family Home Near Everything

3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (22 reviews)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is AU$923
includes taxes & fees
22 Apr - 23 Apr
3 Story Beach Waterview, 3 KING bed, golf putting green!

Waterfront Designer Retreat | Stunning Sunsets! 5 minutes to the beach!

Waterfront Designer Retreat | Stunning Sunsets! 5 minutes to the beach!
Shirley
The price is AU$914
includes taxes & fees
21 Apr - 22 Apr
Waterfront Designer Retreat | Stunning Sunsets! 5 minutes to the beach!

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Rocky Point
10.0 out of 10, Exceptional, (25 reviews)
"It was perfect for what we needed and the hostess made it very simple and easy to check in and check out and answer any questions thank you"
United States
ken g.
The price is AU$757
includes taxes & fees
20 Apr - 21 Apr
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

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

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Brentwood
9.4 out of 10, Exceptional, (39 reviews)
"We had a good experience and we brought our little pup and she was welcome there. Clean and quiet stay "
United States
janice s.
The price is AU$218
includes taxes & fees
19 Apr - 20 Apr
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
10.0 out of 10, Exceptional, (4 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is AU$547
includes taxes & fees
23 Apr - 24 Apr
The Royal Suite - Ronkonkoma

Family-Friendly Retreat w/ Trampoline & Grill

Family-Friendly Retreat w/ Trampoline & Grill
Locust Valley
The price is AU$575
includes taxes & fees
23 Apr - 24 Apr
Family-Friendly Retreat w/ Trampoline & Grill

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Huntington
9.8 out of 10, Exceptional, (7 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is AU$317
includes taxes & fees
11 May - 12 May
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (29 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is AU$1,695
includes taxes & fees
19 Apr - 20 Apr
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (10 reviews)
"Clean and host was very helpful and accommodating. Highly recommend! "
United States
Brenna M.
The price is AU$820
includes taxes & fees
20 Apr - 21 Apr
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
10.0 out of 10, Exceptional, (4 reviews)
"5/5 I enjoyed my stay , very clean and spacious. "
United States
Quywana F.
The price is AU$932
includes taxes & fees
28 Apr - 29 Apr
Modern Vacation home. Close to The Hamptons

Jericho Luxe Retreat

Jericho Luxe Retreat
Jericho
10.0 out of 10, Exceptional, (1 review)
"My family and I had a great stay! Perfect location!"
United States
Maurice Joen R.
Jericho Luxe Retreat

Peaceful private 2-bedroom house in Bayport. Amazing location!

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
10.0 out of 10, Exceptional, (2 reviews)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
United States
Emily D.
The price is AU$327
includes taxes & fees
20 Apr - 21 Apr
Peaceful private 2-bedroom house in Bayport. Amazing location!

Pure Paradise Hamptons Getaway

Pure Paradise Hamptons Getaway
East Patchogue
10.0 out of 10, Exceptional, (1 review)
"Nice house and great pool. "
United States
Bret C.
The price is AU$2,752
includes taxes & fees
20 Apr - 21 Apr
Pure Paradise Hamptons Getaway

Home Away from Home – 3BR Retreat with Amenities

Home Away from Home – 3BR Retreat with Amenities
Hauppauge
10.0 out of 10, Exceptional, (12 reviews)
"Melissa was very accommodating and friendly. The house was as described and a great location to celebrate Christmas with our family."
United States
Andrea A.
The price is AU$814
includes taxes & fees
21 Apr - 22 Apr
Home Away from Home – 3BR Retreat with Amenities

Tranquil Stay

Tranquil Stay
Shirley
8.0 out of 10, Very good, (10 reviews)
"The property was spacious, clean and well kept. We only stayed one night but enjoyed our time. We definitely would stay again. "
United States
Ellen C.
The price is AU$878
includes taxes & fees
18 Apr - 19 Apr
Tranquil Stay

Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (25 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
United States
Maury A.
The price is AU$1,193
includes taxes & fees
19 Apr - 20 Apr
Stylish Beach Home near Stamford Downtown/Beach

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (22 reviews)
"Great location for visiting Stamford, right on the water, a short walk from the beach, a short drive from the ShopRite. Liked the pool table. Excellent kitchen. Backyard seemed very nice but didn't use it due to weather. Easily parks 5 cars, and off-season (Oct-Apr) there is parking at the beach nearby."
United States
Eric K.
The price is AU$1,660
includes taxes & fees
14 May - 15 May
Waterview House Walking Distance from Cove Beach

Bright airy Fair Harbor home with ocean views steps from the soft sandy beach

Bright airy Fair Harbor home with ocean views steps from the soft sandy beach
Fire Island
9.6 out of 10, Exceptional, (4 reviews)
"Perfect Fire Island getaway. Great location and beautiful beach home. Would recommend and love to come back!"
United States
Jessica W.
The price is AU$1,773
includes taxes & fees
19 Apr - 20 Apr
Bright airy Fair Harbor home with ocean views steps from the soft sandy 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

Find out more about Smithtown

Smithtown Holiday Homes information

Number of reviews
257
Accommodation
516 Holiday Homes
Lowest Price
AU$218
Highest Price
AU$2,752

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