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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 £171
includes taxes & fees
14 Apr - 15 Apr
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 £161
includes taxes & fees
31 Mar - 1 Apr
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 £175
includes taxes & fees
4 Apr - 5 Apr
Lovely RV with AC in charming Bethpage a mile from the train to NYC

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)
"Wonderful all-around, clean, definitely a great experience for my first VRBO stay. "
United States
Tyler M.
The price is £137
includes taxes & fees
31 Mar - 1 Apr
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC

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 £127
includes taxes & fees
4 Apr - 5 Apr
1 bedroom 1 bath private entrance

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (83 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is £194
includes taxes & fees
31 Mar - 1 Apr
DUNE Fairfield Beach

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 £170
includes taxes & fees
8 Apr - 9 Apr
South Shore Studio in Mastic

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 £374
includes taxes & fees
30 Mar - 31 Mar
Shop, Hike, Golf & Swim: Inviting Deer Park Escape

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 £137
includes taxes & fees
28 Mar - 29 Mar
Your Perfect Getaway Between Farmingdale & Amityville

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Huntington
9.6 out of 10, Exceptional, (5 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is £161
includes taxes & fees
7 Apr - 8 Apr
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

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 £126
includes taxes & fees
1 Apr - 2 Apr
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

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, (10 reviews)
"This stay was private and comfortable. Checking in was easy with an electronic lock and the host was very communicative with my questions. 2 things to note are that the walls are thin between this unit and the main house so you can indistinctly hear each other, and the mattress is quite hard, but I know some people prefer that. The bathroom is modern and clean and overall everything was easy. "
United States
Zoe P.
The price is £124
includes taxes & fees
29 Mar - 30 Mar
Cozy 1-bedroom apartment in Hicksville 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 £347
includes taxes & fees
30 Mar - 31 Mar
Captain's Cottage - Cold Spring Harbor Water Views

Modern 2 Bed in BlackRock

Modern 2 Bed in BlackRock
Black Rock Historic District
6.8 out of 10, (3 reviews)
"Cozy get away"
United States
Anonymous traveller
The price is £263
includes taxes & fees
9 Apr - 10 Apr
Modern 2 Bed in BlackRock

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 £407
includes taxes & fees
30 Mar - 31 Mar
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

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 £296
includes taxes & fees
8 Apr - 9 Apr
The Royal Suite - Ronkonkoma

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 £199
includes taxes & fees
29 Mar - 30 Mar
Cozy king suite with kitchen and dining area.

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)
"Everything was clean and comfortable, my stay was pleasant and easy. Thank you!"
United States
Jacquelyn C.
The price is £129
includes taxes & fees
9 Apr - 10 Apr
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

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 £381
includes taxes & fees
28 Mar - 29 Mar
Modern Vacation home. Close to The Hamptons

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 £253
includes taxes & fees
7 Apr - 8 Apr
Spacious one Bedroom Apt with private entrance
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 £126 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 Home Located Close to Stony Brook!: This holiday home rental outside of Smithtown offers a patio, a garden and a BBQ to help you feel perfectly comfortable 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 and your friends and family can relax into your holiday with amenities such as a selection of games.

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.