Photo by Doug Kerr

Smithtown Vacation Rentals

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Vacation Rentals in Smithtown

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (49)
"Really liked Dune. I had a great room that was on the other side from Sea Grape - bar that could be loud. I heard noting from room 31. Could walk to Post Rd and the beach. Ocean view from room. "
The price is CA $295
CA $485 total
includes taxes & fees
Mar 15 - Mar 16
DUNE Fairfield Beach

Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

8.2 out of 10, Very good, (44)
"This house was very nice, as pictured or better. Clean, no issues checking in or out. Wagon was there as promised, more bikes than promised, lots of beach towels and chairs provided. The house had two wonderful outdoor second story decks with great views of the water and the ferry dock. Location was perfect, so convenient to ferry and market. Two things not great. Although it had an AC unit in every bedroom that all worked fine which made ground floor cool and comfortable, the main living...
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms

🌞New Listing!! Ocean View Retreat!🌞

9.4 out of 10, Exceptional, (21)
"Quick 2-night stay, couldn’t have been more comfortable. Ocean Beach (town) has everything (one would need for a Fire Island stay), yet the house is beautifully secluded away from it all. The house is well-cared for with delightful details. The view is wonderful. We had everything we needed. Would stay here again in a heartbeat. Thank you!"
🌞New Listing!! Ocean View Retreat!🌞

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (55)
"Great location, very comfortable, nicely decorated, and well stocked re necessities. "
The price is CA $282
CA $592 total
includes taxes & fees
Mar 10 - Mar 11
Captain's Cottage - Cold Spring Harbor Water Views

Cozy Country Cottage #3

10.0 out of 10, Exceptional, (14)
"Very clean and comfortable "
The price is CA $216
CA $411 total
includes taxes & fees
Mar 12 - Mar 13
Cozy Country Cottage #3

fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

10.0 out of 10, Exceptional, (11)
"The property was as advertised. It was clean and there was plenty of room for my family of 4. The place is updated and has large tvs in each room. We all agreed that beds were awesome and made for a great nights sleep. The location was close to major highways, making it easy to get anywhere we needed to go. I would definitely stay here again. Thank you for a great stay!."
fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (28)
"We had 8 people staying in the house. We were in town for a wedding. The house was well fitted for us. Kitchen had all the dishes we needed. Appliances all worked well. Nice walk to the sound. Neighborhood was kind of iffy but we had no problems. "
Cheerful 4 bedrooms residential house.

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

10.0 out of 10, Exceptional, (25)
"stayed here with my parents and 4 other adults to visit my son at stony brook. The house is very clean and well decorated, new kitchen with all the necessary tools. We will stay here again. "
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment

10.0 out of 10, Exceptional, (15)
"We recently had the joy of staying here with family meeting from different parts of New York and New Jersey. House is beautiful, location is quiet and peaceful with a great view of the bay. Nearby to some great Long Island beaches. Loved the pool and amenities of the home. Faraz was an excellent host and extremely responsive to our needs "
The price is CA $896
CA $2,210 total
includes taxes & fees
Mar 13 - Mar 14
Elegant Villa Retreat w/ Pool, 2 Hot Tubs, & Entertainment

20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

8.6 out of 10, Excellent, (10)
"The place was nice for our time with family for a holiday celebration. Our favorite space was the kitchen dining area which was large and well equipped. There was an issue with the heat upstairs; the hosts endeavored to respond to the problem in a timely manner. (Owners were on site for some of our stay, but it did not affect our activities.) Furniture comfortable....most rooms very lightly furnished. I would recommend bringing extra bedding as most beds only had a light quilt without sheets or...
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.

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

9.4 out of 10, Exceptional, (10)
"We were in town for work so didn't spend much time in the house but it was clean, convenient, easy parking, and a great value. "
The price is CA $287
CA $480 total
includes taxes & fees
Mar 10 - Mar 11
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR

8.8 out of 10, Excellent, (9)
"Great host!"
The price is CA $126
CA $220 total
includes taxes & fees
Mar 10 - Mar 11
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR

Waterfront Home w/ Large Deck & Dock on Narrow Bay

9.0 out of 10, Wonderful, (11)
"Beautiful location, property was clean and as listed. We are already thinking of staying another time. Our contract, Chris, was great, friendly and informative."
Waterfront Home w/ Large Deck & Dock on Narrow Bay

Hottub, ⛳️,firepits, heated pool, pool table, Basketball court.

10.0 out of 10, Exceptional, (22)
"My family stayed for a weekend. Lots to do home and went to wineries one day and Top Golf another day. House was clean, plenty to do with pool table and hot tub, firepit list goes on. Very fun great stay!"
Hottub, ⛳️,firepits, heated pool, pool table, Basketball court.

Charming 3-bedroom house with WiFi and AC in Ronkonkoma, Lake views.

Charming 3-bedroom house with WiFi and AC in Ronkonkoma, Lake views.

Luxury and Affordable Family Home

10.0 out of 10, Exceptional, (2)
"My family and I had the pleasure of staying here during the Christmas holidays, and it was an excellent experience. We were especially grateful for the accessibility features, as my grandmother (85 years young), who uses a walker and had recently undergone surgery, was able to comfortably stay on the main floor. The property had just a few steps to enter, and best of all, there was a bedroom and full bathroom on the main level, along with ample room for a walker or wheelchair.The home itself was...
The price is CA $733
CA $1,321 total
includes taxes & fees
Apr 1 - Apr 2
Luxury and Affordable Family Home

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

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

Gatsby's - Heated Plunge Pool & Hot Tub in OBP, Sleeps 24, Steps From The Beach

Gatsby's - Heated Plunge Pool & Hot Tub in OBP, Sleeps 24, Steps From The Beach

Beach Apt. Wineries, Shopping, Dining

6.2 out of 10, (10)
"It was a decent place to stay."
The price is CA $158
CA $351 total
includes taxes & fees
Mar 13 - Mar 14
Beach Apt. Wineries, Shopping, Dining

1856 Trading House close to water

9.4 out of 10, Exceptional, (12)
"Has character, cute. I did hit my head on the Murphy bed, we needed trash bags and forks. Really enjoyed the outdoors fire pit, needed lots of bug spray. Comfortable AC, wish the Bathroom was bigger, kitchen was great."
1856 Trading House close to water
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 types of properties in Smithtown you may be interested in

Hyatt Regency Long Island

3.5 star property
8.2 out of 10, Very good, (1010)
"Never in 45 years have I been to a hotel where you can’t get coffee if you are an early riser. "
The price is CA $171
CA $195 total
includes taxes & fees
Apr 6 - Apr 7
Hyatt Regency Long Island

Hampton Inn Long Island-Brookhaven

2.5 star property
8.6 out of 10, Excellent, (1036)
"Very clean, the people are extremely nice that work here and I would definitely stay here again"
The price is CA $148
CA $169 total
includes taxes & fees
Mar 16 - Mar 17
Hampton Inn Long Island-Brookhaven

Viana Hotel and Spa, Trademark Collection by Wyndham

4.0 star property
8.4 out of 10, Very good, (1012)
"Great stay "
The price is CA $211
CA $236 total
includes taxes & fees
Mar 16 - Mar 17
Viana Hotel and Spa, Trademark Collection by Wyndham
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.

Frequently asked questions

Are there vacation rentals in Smithtown?

Yes, there are vacation rentals in Smithtown close to Blydenburgh County Park, or you can choose a more remote option if you're looking for extra privacy while you relax. Smithtown is known for its lake views.

What are some of the best vacation home rentals in Smithtown?

Fully Modern 3 bedroom 65"smart tvs cable bluetooth speakers etc: This vacation home rental outside of Smithtown offers a balcony, a private yard, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Smithtown?

Family-friendly attractions include Blydenburgh County Park, whereas Nissequogue River is a spot to enjoy the outdoors. Stonebridge Golf Links and Country Club and Caleb Smith State Park are other places to visit while you're in town.

What are vacation rentals like in Smithtown?

Vacation rentals are private properties you can book for a couple days or more in Smithtown. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.