Smithtown Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Smithtown holiday rentals

2 bedrooms, WiFi, bed sheets

Apartment in Smithtown

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
6.8 out of 10, (3 reviews)
"We enjoyed our stay. The apartment was simple, clean, and comfortable. The neighborhood felt safe, and it was easy to call Uber for rides. LIRR access was also convenient, which made traveling to New York City and Stony Brook very manageable. The highlight was the beautiful backyard, which made the place feel relaxing."
United States
Jing L.
The price is HK$1,221
HK$1,761 total
includes taxes & fees
15 Mar - 16 Mar
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Iron/ironing board, free WiFi, bed sheets

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (80 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
1 bedroom, iron/ironing board, free WiFi, bed sheets

Holiday Home in Brentwood

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
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 HK$810
HK$1,327 total
includes taxes & fees
13 Mar - 14 Mar
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Property entrance

Aparthotel in Historic District

Guesthouse at Norwalk Inn
3.5 star property
8.6 out of 10, Excellent, (41 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is HK$2,809
HK$3,230 total
includes taxes & fees
13 Mar - 14 Mar
Guesthouse at Norwalk Inn
1 bedroom, iron/ironing board, free WiFi, bed sheets

Apartment in Huntington Station

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
10.0 out of 10, Exceptional, (7 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is HK$1,526
HK$2,968 total
includes taxes & fees
13 Mar - 14 Mar
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
1 bedroom, iron/ironing board, free WiFi, bed sheets

Apartment in Amityville

Your Perfect Getaway Between Farmingdale & Amityville
9.4 out of 10, Exceptional, (3 reviews)
"Fantastic! Well communicated and perfectly described! Highly recommend and thank you!"
United States
Wayne L.
The price is HK$831
HK$1,664 total
includes taxes & fees
13 Mar - 14 Mar
Your Perfect Getaway Between Farmingdale & Amityville
Smart TV

Apartment in Huntington Station

THE OASIS @ LONG ISLAND
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
The price is HK$1,956
HK$3,835 total
includes taxes & fees
15 Mar - 16 Mar
THE OASIS @ LONG ISLAND
Living area

Aparthotel in Copiague

The Moonrise Motel is a new vacation spot located in the heart of Kismet!
The price is HK$4,029
HK$6,195 total
includes taxes & fees
13 Mar - 14 Mar
The Moonrise Motel is a new vacation spot located in the heart of Kismet!
1 bedroom, WiFi

Apartment in Huntington Station

Luxe Provincial Style Studio w/ Patio & Parking
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is HK$1,526
HK$3,003 total
includes taxes & fees
15 Mar - 16 Mar
Luxe Provincial Style Studio w/ Patio & Parking
Terrace/patio

Holiday Home in Mastic

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
10.0 out of 10, Exceptional, (28 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is HK$3,826
HK$9,082 total
includes taxes & fees
16 Mar - 17 Mar
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Smart TV, books

Holiday Home in Rocky Point

Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
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$2,097
HK$4,255 total
includes taxes & fees
24 Mar - 25 Mar
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
Fridge, microwave, oven, stovetop

Holiday Home in Shirley

Modern Vacation home. Close to The Hamptons
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 HK$1,953
HK$4,002 total
includes taxes & fees
17 Mar - 18 Mar
Modern Vacation home. Close to The Hamptons
Exterior

Apartment in Kings Park

Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
10.0 out of 10, Exceptional, (18 reviews)
"Perfect spot for a quick trip"
United States
James P.
The price is HK$968
HK$1,419 total
includes taxes & fees
14 Mar - 15 Mar
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
Marina

Holiday Home in Cold Spring Harbor

Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (75 reviews)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
The price is HK$1,698
HK$3,852 total
includes taxes & fees
24 Mar - 25 Mar
Captain's Cottage - Cold Spring Harbor Water Views
Outdoor spa tub

Holiday Home in Commack

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay"
United States
Kenneth B.
The price is HK$3,705
HK$5,816 total
includes taxes & fees
15 Mar - 16 Mar
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Smart TV

Holiday Home in Lake Grove

Spacious Home Located Close to Stony Brook!
7.6 out of 10, Good, (26 reviews)
"Amazing host and amazing house. Thank you!!"
United States
AJ L.
The price is HK$2,105
HK$4,926 total
includes taxes & fees
16 Mar - 17 Mar
Spacious Home Located Close to Stony Brook!
Dining

Apartment in Historic District

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
The price is HK$1,894
HK$2,421 total
includes taxes & fees
16 Mar - 17 Mar
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Microwave, stovetop

Mobile Home in Bethpage

Lovely RV with AC in charming Bethpage a mile from the train to NYC
7.0 out of 10, Good, (4 reviews)
"Super convenient and the host was very responsive. I highly recommend."
United States
Andrew B.
The price is HK$1,056
HK$1,799 total
includes taxes & fees
15 Mar - 16 Mar
Lovely RV with AC in charming Bethpage a mile from the train to NYC
Interior

Apartment in Deer Park

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
The price is HK$861
HK$3,963 total
includes taxes & fees
30 Mar - 31 Mar
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
Interior

Apartment in Syosset

1-bedroom apartment with AC in Syosset
The price is HK$1,267
HK$3,616 total
includes taxes & fees
22 Mar - 23 Mar
1-bedroom apartment with AC in Syosset
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
"Breakfast had good selection and fresh .staff was helpful and hotel was clean"
JOHN 5-night trip
Posted 5 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:

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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?

Luxury Waterfront Retreat • Private Hot Tub & Dock Near Sayville: This holiday home rental outside of Smithtown is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and 1 hot tub.

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.