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 €192
includes taxes & fees
31 Jan - 1 Feb
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

Tiny Home Private, Students, Nurses, Tech

Tiny Home Private, Students, Nurses, Tech
Bay Shore
8.6 out of 10, Excellent, (7 reviews)
"We wanted an inexpensive place to stay out on Long Island for July 4th weekend. We were a 15-20 minute drive to the beautiful beaches of Robert Moses and a 2 hour drive from Montauk.We were able to stay for a very reasonable price over a notoriously expensive weekend.Jenelle's communication was direct, welcoming and helpful.We would definitely stay here again!"
United States
Melanie M.
The price is €172
includes taxes & fees
8 Feb - 9 Feb
Tiny Home Private, Students, Nurses, Tech

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 €197
includes taxes & fees
31 Jan - 1 Feb
Lovely RV with AC in charming Bethpage a mile from the train to NYC

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (78 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

JC Entire Apartment remodeled, close to Airport and Ferry

JC Entire Apartment remodeled, close to Airport and Ferry
Coram
10.0 out of 10, Exceptional, (3 reviews)
"Would definitely stay again "
United States
Katherine R.
The price is €171
includes taxes & fees
2 Feb - 3 Feb
JC Entire Apartment remodeled, close to Airport and Ferry

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 €345
includes taxes & fees
31 Jan - 1 Feb
Guesthouse at Norwalk Inn

The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
10.0 out of 10, Exceptional, (4 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is €297
includes taxes & fees
1 Mar - 2 Mar
The Royal Suite - Ronkonkoma

Walk to Beach 2BR Near Dining & Shopping

Walk to Beach 2BR Near Dining & Shopping
Rocky Point
6.8 out of 10, (27 reviews)
"This is an adequate place to stay. That's about it"
United States
Maureen T.
The price is €187
includes taxes & fees
31 Jan - 1 Feb
Walk to Beach 2BR Near Dining & Shopping

Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
7.8 out of 10, Good, (10 reviews)
"I answered this. Safe and Quit."
United States
John
The price is €284
includes taxes & fees
31 Jan - 1 Feb
Spacious one Bedroom Apt with private entrance

South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (3 reviews)
"Great stay! Super comfy and clean😊"
United States
ERIN
The price is €192
includes taxes & fees
31 Jan - 1 Feb
South Shore Studio in Mastic

Peaceful private 2-bedroom house in Bayport.Amazing location!

Peaceful private 2-bedroom house in Bayport.Amazing location!
Bayport
10.0 out of 10, Exceptional, (1 review)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
United States
Emily D.
The price is €242
includes taxes & fees
1 Feb - 2 Feb
Peaceful private 2-bedroom house in Bayport.Amazing location!

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, (13 reviews)
"Clean, comfortable and safe. Stayed overnight with my Son for a show at Nassau Veterans Colliseum the following day. Stew Leonard's in walking distance was perfect for cooking our dinner with the fully stocked kitchen here. I would definitely stay here again. Thank you "
United States
Brian S.
The price is €125
includes taxes & fees
1 Feb - 2 Feb
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

Cozy 2 bedroom retreat in long island

Cozy 2 bedroom retreat in long island
Central Islip
7.0 out of 10, Good, (4 reviews)
"Apt was clean and comfortable. Beds were comfortable. Area was nice. Owner communication was good. Only drawback is the plumbing situation was not advertised in the listing. Iif you are comfortable using a bidet and not flushing paper, this apt is perfect. "
United States
Deborah R.
The price is €228
includes taxes & fees
31 Jan - 1 Feb
Cozy 2 bedroom retreat in long island

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, (17 reviews)
"Overall, a great crash pad. Hosts were great with communication and convenience. Location was convenient, clean, and comfortable. "
United States
Erika K.
The price is €156
includes taxes & fees
1 Feb - 2 Feb
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

Cozy Country Cottage #4

Cozy Country Cottage #4
Miller Place
10.0 out of 10, Exceptional, (15 reviews)
"Great stay"
United States
Susan W.
Cozy Country Cottage #4

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 €168
includes taxes & fees
31 Jan - 1 Feb
1 bedroom 1 bath private entrance

3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!
Shirley
10.0 out of 10, Exceptional, (22 reviews)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year! "
United States
Red F.
The price is €514
includes taxes & fees
1 Feb - 2 Feb
3 Story Beach Waterview, 3 KING bed, golf putting green!

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
9.2 out of 10, Wonderful, (9 reviews)
"Nice location, clean and comfortable, and looking forward to possibly revisiting."
United States
Doug S.
The price is €134
includes taxes & fees
10 Feb - 11 Feb
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

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, (38 reviews)
"Very convenient location for where I needed to be. Perfect room to stay for a night "
United States
Sophie B.
The price is €146
includes taxes & fees
1 Feb - 2 Feb
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Cozy king suite with kitchen and dining area.

Cozy king suite with kitchen and dining area.
Coram
9.4 out of 10, Exceptional, (6 reviews)
"Very clean and well kept property. Easy communication with ow er/manager"
United States
Tasia P.
The price is €225
includes taxes & fees
31 Jan - 1 Feb
Cozy king suite with kitchen and dining area.
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 €125 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?

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.: This holiday home rental outside of Smithtown is located by the ocean, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a pool table and 1 hot tub so that you can immerse yourself in your holiday.

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 Smithaven Mall 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.