Holiday Rentals in Smithtown

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Our top choices for Smithtown holiday rentals

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

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
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 €200
includes taxes & fees
10 Apr - 11 Apr
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (80 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is €234
includes taxes & fees
22 Mar - 23 Mar
DUNE Fairfield Beach

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, (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 €153
includes taxes & fees
17 Mar - 18 Mar
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
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 €362
includes taxes & fees
17 Mar - 18 Mar
Guesthouse at Norwalk Inn

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (7 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is €331
includes taxes & fees
7 Apr - 8 Apr
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
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 €190
includes taxes & fees
17 Mar - 18 Mar
Your Perfect Getaway Between Farmingdale & Amityville

THE OASIS @ LONG ISLAND

THE OASIS @ LONG ISLAND
Huntington Station
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
The price is €423
includes taxes & fees
22 Mar - 23 Mar
THE OASIS @ LONG ISLAND

The Moonrise Motel is a new vacation spot located in the heart of Kismet!

The Moonrise Motel is a new vacation spot located in the heart of Kismet!
Copiague
The price is €703
includes taxes & fees
13 Apr - 14 Apr
The Moonrise Motel is a new vacation spot located in the heart of Kismet!

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
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 €337
includes taxes & fees
17 Mar - 18 Mar
Luxe Provincial Style Studio w/ Patio & Parking

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
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 €1,036
includes taxes & fees
23 Mar - 24 Mar
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

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 €465
includes taxes & fees
17 Mar - 18 Mar
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

Modern Vacation home. Close to The Hamptons

Modern Vacation home. Close to The Hamptons
Shirley
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 €446
includes taxes & fees
20 Mar - 21 Mar
Modern Vacation home. Close to The Hamptons

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, (18 reviews)
"Perfect spot for a quick trip"
United States
James P.
The price is €163
includes taxes & fees
17 Mar - 18 Mar
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
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 €413
includes taxes & fees
23 Mar - 24 Mar
Captain's Cottage - Cold Spring Harbor Water Views

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Commack
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay"
United States
Kenneth B.
The price is €649
includes taxes & fees
19 Mar - 20 Mar
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

Spacious Home Located Close to Stony Brook!

Spacious Home Located Close to Stony Brook!
Lake Grove
7.6 out of 10, Good, (26 reviews)
"Amazing host and amazing house. Thank you!!"
United States
AJ L.
Spacious Home Located Close to Stony Brook!

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
The price is €273
includes taxes & fees
17 Mar - 18 Mar
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

Lovely RV with AC in charming Bethpage a mile from the train to NYC

Lovely RV with AC in charming Bethpage a mile from the train to NYC
Bethpage
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 €206
includes taxes & fees
17 Mar - 18 Mar
Lovely RV with AC in charming Bethpage a mile from the train to NYC

Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
The price is €444
includes taxes & fees
30 Mar - 31 Mar
Shop, Hike, Golf & Swim: Inviting Deer Park Escape

1-bedroom apartment with AC in Syosset

1-bedroom apartment with AC in Syosset
Syosset
The price is €400
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

Find out more about Smithtown

Everything you need to know about Smithtown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Smithtown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Smithtown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Smithtown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Smithtown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Smithtown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Smithtown holiday rentals we have selected for you start as low as €153 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Smithtown rentals

At Expedia, we put the best Smithtown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Smithtown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Smithtown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Smithtown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Adorable Cottage with Water Views, Across the street from Prime & other eateries: This holiday home rental outside of Smithtown is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 Avalon Park and Preserve are a couple of places you'll find in the wider area.

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.