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Compare 471 Vacation Homes in Smithtown with updated reviews, rates, and availability.

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

8.2 out of 10, Very Good, (44)
"This house was in the perfect location as it was close to the ferry terminal and a short walk to ocean beach."
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (58)
"Everything was awesome! Would definitely stay here again! "
The price is AED 1,359
AED 2,543 total
includes taxes & fees
15 May - 16 May
Captain's Cottage - Cold Spring Harbor Water Views

🌞New Listing!! Ocean View Retreat!🌞

9.4 out of 10, Exceptional, (21)
"Loved the bamboo flanked boardwalk getting to the cottage. Cute cottage with an amazing beach view"
🌞New Listing!! Ocean View Retreat!🌞

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (30)
"Great communication and accommodations from the host. We were in town for a concert and the location couldn't have been better! Would recommend this stay for anyone looking within the area."
Cheerful 4 bedrooms residential house.

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

10.0 out of 10, Exceptional, (26)
"Great place to stay. It was prefect for our family of six. We really enjoyed the stay and would stay there again. It was very clean and organized."
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Luxury and Affordable Family Home

10.0 out of 10, Exceptional, (2)
"Had a 2 night stay. Was a recently renovated house. Beautifully designed."
The price is AED 1,873
AED 3,760 total
includes taxes & fees
27 Apr - 28 Apr
Luxury and Affordable Family Home

Home away from home

10.0 out of 10, Exceptional, (9)
"We will definitely be making another trip! Very clean and had everything we needed for our home away from home weekend!"
Home away from home

The Raabbit Hole

9.2 out of 10, Wonderful, (22)
"Only recommendation would be to upgrade the beach chairs . The house was very Homie and comfortable and plenty big. Would definitely stay again. "
The Raabbit Hole

Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

9.4 out of 10, Exceptional, (10)
"Perfect residential home to stay at"
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

Hottub, ⛳️, htd pool,Basketball, volleyball . 10% book 2 nights

10.0 out of 10, Exceptional, (22)
"It was a very nice experience staying there. The owner replied to our questions pretty fast. I love the backyard, but unfortunately, it is too cold to stay outside during the winter. I would definitely recommend this house and we will try and go back in a warmer season!"
The price is AED 2,204
AED 4,792 total
includes taxes & fees
10 May - 11 May
Hottub, ⛳️, htd pool,Basketball, volleyball . 10% book 2 nights

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

9.8 out of 10, Exceptional, (6)
"Cute little condo that was located very close to lots of restaurants, the supermarket, and everything that you can need/want on a trip. Would stay here again. "
Walkable to all in Downtown Seaford! Clean 1 bed basement unit

Beach Bungalow Ocean Beach

9.8 out of 10, Exceptional, (22)
"This was our second year with this house. Everything was great. We will be back next year for a third year. "
Beach Bungalow Ocean Beach

Spacious beach cottage with private pool, hot tub, outdoor area & amazing suite

8.8 out of 10, Excellent, (20)
"The house was clean. Great communication with host. Would stay again!"
Spacious beach cottage with private pool, hot tub, outdoor area & amazing suite

Fire Island Beach House - Atlantique

9.8 out of 10, Exceptional, (10)
"Location was perfect as a very short walk from Ferry port. Views over bay, was beautiful. Very well looked after by the owner. Had a wonderful time. 😊"
Fire Island Beach House - Atlantique

Mastic Beach Surf House

10.0 out of 10, Exceptional, (10)
"The house was relaxing and cozy. The perfect quiet get-away from the hustle and bustle of the city!!"
Mastic Beach Surf House

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

10.0 out of 10, Exceptional, (12)
"All went well, would stay again if in the area"
The price is AED 1,028
AED 2,014 total
includes taxes & fees
30 Apr - 1 May
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Spacious Gorgeous Getaway perfect for family reunion or business

9.8 out of 10, Exceptional, (6)
"House was perfect for the group. We had everything we needed and plenty of room for us. Owner was great with communications before and during our stay"
Spacious Gorgeous Getaway perfect for family reunion or business

Breathtaking Waterfront house

9.4 out of 10, Exceptional, (3)
"Fun property, kitchen needs a little organizing, And instructions for tv and remotes would be helpful"
Breathtaking Waterfront house

Beautiful 3 BR Full House w/ King Bed on Dead End- 5 min from town!

9.6 out of 10, Exceptional, (12)
"Benny's house was a convenient and comfortable spot for our brief stay in the area, and the logistics couldn't have been easier."
Beautiful 3 BR Full House w/ King Bed on Dead End- 5 min from town!

Charming Long Island Home Near Beaches & Golf

9.6 out of 10, Exceptional, (7)
"Simple and clean home. Very convenient location."
Charming Long Island Home Near Beaches & Golf
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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Other property types in Smithtown

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

The price is AED 573
AED 823 total
includes taxes & fees
27 Apr - 28 Apr
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (52)
"Absolutely perfect location for visiting Fairfield University! Everything about it exceeded our expectations."
The price is AED 1,606
AED 2,049 total
includes taxes & fees
2 May - 3 May
DUNE Fairfield Beach

Luxury and Affordable Family Home

10.0 out of 10, Exceptional, (2)
"Had a 2 night stay. Was a recently renovated house. Beautifully designed."
The price is AED 1,873
AED 3,760 total
includes taxes & fees
27 Apr - 28 Apr
Luxury and Affordable Family Home
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.