Beautiful golden hour sunrise on the beach at Kings Park Bluffs and Sunken Meadow State Park in Smithtown, NY at dawn. Hot, summer day. Clear, no clouds. Blue sky, coastline of Long Island Sound.

Smithtown Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Smithtown holiday rentals

Terrace/patio

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is HK$987
HK$1,904 total
includes taxes & fees
16 Jun - 17 Jun
Spacious 3BR Family Home Near Everything
Interior

Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Easy to get to. Listing as described. Bed and furniture are nice and comfy. Only thing I would add is a broom and dust pain and some Clorox wipes so guest can keep it neat. 5 stars! Very nice host. "
United States
Samantha
The price is HK$1,152
HK$2,480 total
includes taxes & fees
27 Jun - 28 Jun
Sundown Escape-South Shore Long Island
Outdoor dining

Cozy 1BR Artist Den Near Oheka Castle & Huntington Village

Cozy 1BR Artist Den Near Oheka Castle & Huntington Village
Huntington
9.6 out of 10, Exceptional, (8 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is HK$1,136
HK$1,746 total
includes taxes & fees
8 Jul - 9 Jul
Cozy 1BR Artist Den Near Oheka Castle & Huntington Village
Shower, hair dryer, towels, soap

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, (44 reviews)
"This place was the perfect location for us. Almost exact center between Jones beach and Port Jefferson. Clean and identical to what is shown."
United States
Marcus
The price is HK$846
HK$1,370 total
includes taxes & fees
16 Jun - 17 Jun
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Exterior detail

East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!
East Meadow
8.8 out of 10, Excellent, (15 reviews)
"Cute little apt . Perfect location highly recommend"
United States
Kristin
The price is HK$744
HK$1,268 total
includes taxes & fees
16 Jun - 17 Jun
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!
Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (91 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is HK$1,506
HK$2,210 total
includes taxes & fees
29 Jun - 30 Jun
DUNE Fairfield Beach
1 bedroom, free WiFi, bed sheets

South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (4 reviews)
"Really nice and great price! Would stay again. "
United States
Philip P.
The price is HK$1,058
HK$1,790 total
includes taxes & fees
5 Jul - 6 Jul
South Shore Studio in Mastic
Hair dryer, towels, soap, toilet paper

Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (6 reviews)
"The whole experience was great"
United States
David
The price is HK$1,114
HK$2,061 total
includes taxes & fees
16 Jun - 17 Jun
Your Perfect Getaway Between Farmingdale & Amityville
Towels, soap, shampoo, toilet paper

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
8.8 out of 10, Excellent, (11 reviews)
"Had a great stay "
United States
Desiree
The price is HK$712
HK$1,232 total
includes taxes & fees
17 Jun - 18 Jun
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Exterior

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Kings Park
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is HK$1,058
HK$1,522 total
includes taxes & fees
13 Jul - 14 Jul
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
TV

Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
7.8 out of 10, Good, (10 reviews)
"The place was great. It was clean and spacious, and located on a quiet street. It was also accessible to all the major roads. The host was very accommodating. Very pleased with it all and would highly recommend! "
United Kingdom
Selective Travel M.
The price is HK$881
HK$2,690 total
includes taxes & fees
22 Jun - 23 Jun
Spacious one Bedroom Apt with private entrance
Interior

Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.6 out of 10, Exceptional, (7 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is HK$1,371
HK$2,104 total
includes taxes & fees
22 Jun - 23 Jun
Cozy king suite with kitchen and dining area.
Smart TV, table football, books, stereo

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 HK$2,100
HK$4,279 total
includes taxes & fees
22 Jun - 23 Jun
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Interior

Private 1 bedroom apt in a quiet neighborhood, close to all!

Private 1 bedroom apt in a quiet neighborhood, close to all!
Centereach
9.6 out of 10, Exceptional, (26 reviews)
"It was the perfect landing pad for a family reunion. We hope to stay there again next year."
United States
Amanda
The price is HK$1,849
HK$2,927 total
includes taxes & fees
5 Jul - 6 Jul
Private 1 bedroom apt in a quiet neighborhood, close to all!
1 bedroom, WiFi, bed sheets

1 bedroom 1 bath private entrance

1 bedroom 1 bath private entrance
Bay Shore
8.8 out of 10, Excellent, (22 reviews)
"Well suited for our needs."
United States
Teresa D.
The price is HK$846
HK$1,468 total
includes taxes & fees
23 Jun - 24 Jun
1 bedroom 1 bath private entrance
Fridge, microwave, coffee/tea maker, electric kettle

Sundown Escape Near SouthShore University Hospital

Sundown Escape Near SouthShore University Hospital
Bay Shore
The price is HK$1,128
HK$2,710 total
includes taxes & fees
27 Jun - 28 Jun
Sundown Escape Near SouthShore University Hospital
Pool

Tiny Home Private, Students, Nurses, Tech

Tiny Home Private, Students, Nurses, Tech
Bay Shore
7.8 out of 10, Good, (8 reviews)
"Great host, nice place."
United States
Brian C.
The price is HK$1,638
HK$2,577 total
includes taxes & fees
21 Jun - 22 Jun
Tiny Home Private, Students, Nurses, Tech
Property grounds

Walk to Beach 2BR Near Dining & Shopping

Walk to Beach 2BR Near Dining & Shopping
Rocky Point
6.8 out of 10, (30 reviews)
"Host was very welcoming and helpful! "
United States
Alissa I.
The price is HK$1,234
HK$2,636 total
includes taxes & fees
17 Jun - 18 Jun
Walk to Beach 2BR Near Dining & Shopping
Fridge, microwave, oven, stovetop

Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
7.6 out of 10, Good, (4 reviews)
"Cute and efficient property, and a great location. The host was very prompt with any and all questions. Definitely recommend the place for a quick get away."
United States
Joshua L.
The price is HK$1,381
HK$3,051 total
includes taxes & fees
17 Jun - 18 Jun
Modern 2 Bed in BlackRock
Coffee/tea maker, spices

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
The price is HK$1,606
HK$3,124 total
includes taxes & fees
16 Jun - 17 Jun
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
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

Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

10/10 Excellent
"Great experience"
Ashton 2-night trip
Posted 2 hours ago
Hampton Inn Long Island-Brookhaven

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
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  • 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?

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. : 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 fridge, a microwave and a coffee maker.

What can I see and do in Smithtown?

Nissequogue River and Caleb Smith State Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Blydenburgh County Park. Stonebridge Golf Links and Country Club and paces steakhouse 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.