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Smithtown Holiday Rentals

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Check prices for these dates

In two weeks
26 Sept - 28 Sept
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec
In four months
2 Jan - 4 Jan

Holiday Rentals in Smithtown

Our top choices for Smithtown holiday rentals

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

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

5.0 out of 10, (2)
"Overall clean space and super easy check in/out. Location is on a quiet street/neighborhood which is nice. Not full a/c in rooms but had two floor fans; was hot in summertime but manageable for a short stay. Had a nice deadbolt on door to lock it. Awkward entrance as you go through the back of the house and all the way around the property, but it isn't terrible. A bit of a dead zone for Verizon but T-mobile was OK; Wi-Fi was available which was needed. Good for easy overnight stay and cheaper...
The price is HK$1,216
HK$1,790 total
includes taxes & fees
19 Sept - 20 Sept
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
DUNE Fairfield Beach
Private beach nearby, sun-loungers, beach umbrellas, beach towels

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (69)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach
Guesthouse at Norwalk Inn
Property entrance

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
The price is HK$2,174
HK$2,500 total
includes taxes & fees
14 Sept - 15 Sept
Guesthouse at Norwalk Inn
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Beach

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

10.0 out of 10, Exceptional, (2)
"Friendly host, very good location and a simple check-in process. Few minutes drive to the beach. "
The price is HK$2,065
HK$2,840 total
includes taxes & fees
1 Oct - 2 Oct
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Newly Renovated Luxury Beach House Ocean Bay Park
Outdoor dining

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (69)
"Very nice place for a family to stay"
The price is HK$5,447
HK$9,910 total
includes taxes & fees
29 Sept - 30 Sept
Newly Renovated Luxury Beach House Ocean Bay Park
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC
Terrace/patio

Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

8.8 out of 10, Excellent, (8)
"Very cute cottage on the water with a deck and beautiful views. A short walk into town to shops and restaurants. "
The price is HK$3,102
HK$5,556 total
includes taxes & fees
20 Sept - 21 Sept
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC
Spacious Home Located Close to Stony Brook!
Property grounds

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (19)
"Great stay great people great costumer care definitely reccomend"
Spacious Home Located Close to Stony Brook!
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR
Dining

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

9.2 out of 10, Wonderful, (15)
"The property was very quaint and comfortable. We'll probably stay again in the future"
The price is HK$643
HK$1,168 total
includes taxes & fees
13 Sept - 14 Sept
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bedroom, iron/ironing board, free WiFi, bed sheets

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

9.4 out of 10, Exceptional, (26)
"its small but very nice for a short stay would recommend."
The price is HK$772
HK$1,282 total
includes taxes & fees
10 Sept - 11 Sept
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bed room basement apartment.
Microwave, stovetop

1 bed room basement apartment.

8.2 out of 10, Very good, (10)
"The property was very spacious and can bring family there. "
The price is HK$779
HK$1,305 total
includes taxes & fees
21 Sept - 22 Sept
1 bed room basement apartment.
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
1 bedroom, in-room safe, desk, free WiFi

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

9.4 out of 10, Exceptional, (6)
"Had a great stay "
The price is HK$701
HK$1,218 total
includes taxes & fees
12 Sept - 13 Sept
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC
Microwave, oven, stovetop, dishwasher

Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC

2.0 out of 10, (1)
"While we received multiple confirmations of our reservation, including the morning we were to check in, the property manager never sent us check in instructions, even after we emailed asking for them. Then, after spending over an hour with multiple calls to VRBO customer service, who also couldn’t get ahold of the property manager, we arrived at the location. There was a 4ft high, 10ft wide heap of garbage in the front yard and looking in through the windows it was apparent the house was under...
The price is HK$6,234
HK$8,325 total
includes taxes & fees
15 Sept - 16 Sept
Spacious 5-bedroom villa in pleasant Setauket- East Setauket with WiFi, AC
Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow
Property grounds

Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow

9.8 out of 10, Exceptional, (8)
"Perfect location to enjoy Northport! Everything is within walking distance. Host was very helpful and accommodating. Great stay and will definitely return! "
The price is HK$5,520
HK$9,218 total
includes taxes & fees
18 Sept - 19 Sept
Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow
Weekends, midweeks and full weeks available! Steps to Beach, town and ferries!
Beach nearby

Weekends, midweeks and full weeks available! Steps to Beach, town and ferries!

9.8 out of 10, Exceptional, (21)
"Great time...close to the beach or the bay"
Weekends, midweeks and full weeks available! Steps to Beach, town and ferries!
Tiny Home Private, Students, Nurses, Tech
Property grounds

Tiny Home Private, Students, Nurses, Tech

9.4 out of 10, Exceptional, (3)
"I was very pleased with the property, and the host made me feel more than welcome."
The price is HK$814
HK$1,571 total
includes taxes & fees
17 Sept - 18 Sept
Tiny Home Private, Students, Nurses, Tech
Walk to Beach 2BR Near Dining & Shopping
Property grounds

Walk to Beach 2BR Near Dining & Shopping

6.4 out of 10, (19)
"The beach is private and you need to be a Brookhaven resident to be admitted. This is not specified anywhere on the listing. Communication about this with the owner via app was rather poor. "
The price is HK$1,087
HK$2,373 total
includes taxes & fees
10 Sept - 11 Sept
Walk to Beach 2BR Near Dining & Shopping
Chic Private 1BR Suite/Walk to Shops
Property grounds

Chic Private 1BR Suite/Walk to Shops

9.0 out of 10, Wonderful, (2)
"Vanessa is very responsive and laid back. She made the booking and check-in process seamless and the location of her property is stellar. The neighborhood is great to walk dogs and safe. "
The price is HK$1,753
HK$2,236 total
includes taxes & fees
10 Sept - 11 Sept
Chic Private 1BR Suite/Walk to Shops
Modern Vacation home. Close to The Hamptons
Fridge, microwave, oven, stovetop

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is HK$2,591
HK$4,910 total
includes taxes & fees
10 Sept - 11 Sept
Modern Vacation home. Close to The Hamptons
1 bedroom 1 bath private entrance
Interior

1 bedroom 1 bath private entrance

8.8 out of 10, Excellent, (20)
"Just as pictured! Lovely studio apartment which was absolutely beautiful and comfortable. Great location, nice quiet neighborhood, and ample parking.I will definitely stay again! Thank you so much!"
The price is HK$982
HK$1,612 total
includes taxes & fees
10 Sept - 11 Sept
1 bedroom 1 bath private entrance
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
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

Find out more about Smithtown

Search for holiday rentals in Smithtown on Expedia! You can easily find your home rentals, villas, holiday apartments in Smithtown using one of the methods below:

  • View our selection of featured holiday rentals in Smithtown
  • Use the map to find apartments and other holiday homes in the Smithtown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Smithtown while they last

Look no further and take a look at our great range of rental properties in Smithtown!

Frequently asked questions

Are there holiday rentals in Smithtown?

Yes, there are holiday rentals in Smithtown close to Blydenburgh County Park, or you can select a more secluded option if you're looking for a relaxing stay. Smithtown is known for its lake views.

What are some of the best holiday rentals that Smithtown has to offer?

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.: This holiday home rental outside of Smithtown has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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 holiday rentals like in Smithtown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Smithtown. Holiday rentals feature amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for small groups.