Smithtown holiday homes

We found 190 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Smithtown to find one that's perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you expect for your stay, which might include a garden and hot tub. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Smithtown

Showing deals for:18 Dec - 25 Dec

Outdoor dining
Interior
Dining
Property grounds
Exceptional
(15 reviews)

The President Mansion Luxurious Family Retreat - 1.5 Miles to Beach

Bay Shore

8% off
NZ$31,004
for 7 nights, 1 home
NZ$4,429 per night
includes taxes & fees
The President Mansion Luxurious Family Retreat - 1.5 Miles to Beach
Bar (on property)
Dining
Golf
Room
Exceptional
(71 reviews)

Northport quaint restored Boathouse with sunset views!

Northport

8% off
NZ$5,280
for 7 nights, 1 cottage
NZ$754 per night
includes taxes & fees
Northport quaint restored Boathouse with sunset views!
Nice place for Breakfast in the sunroom
view as you walk into sunroom
lower bedroom with walk in closet and king size tempurpedic bed
Door to outside, Like the flowers?
Exceptional
(59 reviews)

1856 Trading House w/ walk to water

Mount Sinai

12% off
NZ$3,707
for 7 nights, 1 apartment
NZ$530 per night
includes taxes & fees
1856 Trading House w/ walk to water
Interior
Private kitchen
Living area
Dining
Exceptional
(30 reviews)

Relax or Work While Away

Deer Park

8% off
NZ$6,644
for 7 nights, 1 home
NZ$949 per night
includes taxes & fees
Relax or Work While Away
Interior
Interior
Interior
Interior
Exceptional
(32 reviews)

1856 Trading House close to water

Mount Sinai

12% off
NZ$3,707
for 7 nights, 1 apartment
NZ$530 per night
includes taxes & fees
1856 Trading House close to water
Living area
Room
Room
Bathroom
Exceptional
(52 reviews)

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

Brentwood

8% off
NZ$1,765
for 7 nights, 1 home
NZ$252 per night
includes taxes & fees
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Exterior
Private kitchen
Living area
Living area
Exceptional
(59 reviews)

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Centereach

8% off
NZ$7,595
for 7 nights, 1 home
NZ$1,085 per night
includes taxes & fees
Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

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    Enjoy full kitchens, laundry, pools, gardens and more

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    More space, more privacy, more amenities — more value

Take in the natural beauty of Smithtown

The wildlife, island views and lake are the perfect backdrop to your holiday home in Smithtown. Travellers appreciate the bird watching in this romantic city. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in Smithtown

Do you want to find attractions to visit while you're in the area? Venture out of your holiday home and experience everything that makes Smithtown a fun spot to go on holiday. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Stonebridge Golf Links and Country Club (2.1 mi / 3.3 km)
  • Adventureland (13.5 mi / 21.7 km)
  • Cold Spring Harbor Laboratory (14 mi / 22.6 km)
  • Oyster Bay Golf Course (14.9 mi / 24 km)
  • Bethpage Black State Park Golf Course (15.5 mi / 24.9 km)
  • Bethpage Black (15.7 mi / 25.2 km)

Exploring the natural landscape of Smithtown

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Smithtown is a great place to get outside. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Avalon Park and Preserve (4.5 mi / 7.2 km)
  • Lake Ronkonkoma (4.7 mi / 7.6 km)
  • Islip Town Beach (10.4 mi / 16.7 km)
  • Fire Island National Seashore (11.9 mi / 19.1 km)
  • Shorefront Park (12.6 mi / 20.2 km)
  • Cold Spring Harbor State Park (13.5 mi / 21.6 km)

Transport to and around Smithtown

Fly into Islip, NY (ISP-MacArthur), the closest airport, located 7.1 mi (11.4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Farmingdale, NY (FRG-Republic), which is 14.4 mi (23.2 km) away.

If you'd rather travel by train, you can make your way to Smithtown Station.

Frequently asked questions

What is the best area to stay in Smithtown when booking a holiday rental?
When booking a holiday rental in Smithtown, New York, a great area to consider is the vicinity around the picturesque Smithtown Village. This charming neighbourhood boasts a variety of lovely properties, ranging from cosy cottages to larger family homes, making it quite appealing for visitors seeking both comfort and convenience.Within Smithtown Village, you can enjoy the delightful atmosphere of local shops, cafes, and restaurants, great for immersing yourself in the community's vibe. A highlight of the area is the expansive Blydenburgh County Park, where you can explore scenic trails, picnic areas, and even a lovely lake ideal for kayaking or fishing. Additionally, the nearby Long Island Museum offers insights into the region's rich history and features fascinating exhibits on art and culture.Another attractive option is the area near the Smithtown Historical Society, where you can find a range of properties that provide easy access to local attractions. The Historical Society itself is a wonderful place to learn about Smithtown's past and participate in various events throughout the year.
What is the most popular type of holiday rental accomodation in Smithtown?
In Smithtown, apartments are the most popular type of holiday rental, with several available throughout the area. These apartments typically provide a homely atmosphere, featuring fully equipped kitchens, comfortable living spaces, and modern amenities. Travellers can expect convenient access to local attractions, parks, and restaurants, making them ideal for both short and extended stays.
Are there any family house rentals in Smithtown?
In Smithtown, New York, several family-friendly rentals can be found, making it a great choice for those travelling with children. The area offers spacious homes equipped with amenities that cater to families, such as fully equipped kitchens for preparing meals and comfortable living areas for relaxation. Many properties also feature outdoor spaces, superb for kids to play or for family gatherings.Visitors can explore nearby attractions like the expansive Caleb Smith State Park, which provides opportunities for hiking and picnicking, and the charming local shops and restaurants that add to the family-friendly atmosphere.
Are there pet-friendly house rentals in Smithtown?
In Smithtown, there are several pet-friendly house rentals available, suiting those travelling with pets. Visitors can expect homes that offer amenities such as fenced yards, spacious living areas, and fully equipped kitchens, making them ideal for families or groups. Many properties also feature outdoor spaces, superb for pets to enjoy fresh air and playtime.The neighbourhood itself provides a charming suburban atmosphere, with nearby parks that are suitable for walks and playtime with pets. Smithtown's quiet streets and local parks create a welcoming environment for pet owners looking to explore the area.
Are there any remote work holiday rentals in Smithtown?
In Smithtown, New York, there are several remote work-friendly holiday rentals available. The area offers a variety of properties that cater to those needing a comfortable workspace while enjoying their stay. Many of these rentals come equipped with reliable Wi-Fi, ensuring that guests can work efficiently. Additionally, properties often feature dedicated workspaces or quiet areas conducive to productivity, along with amenities like fully equipped kitchens and spacious living areas for relaxation after work hours.Smithtown itself is a charming town with local parks and restaurants, providing a pleasant environment for remote workers to balance work and leisure. Whether guests prefer a modern apartment or a cozy house, there are options available that suit different preferences and group sizes. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Smithtown?
In Smithtown, popular holiday rental amenities include well-equipped kitchens, allowing guests to prepare their own meals during their stay. Many rentals also feature coffee and tea makers for a convenient morning brew. Outdoor spaces such as decks or patios are common, providing a lovely setting for relaxation or outdoor dining. Additionally, dining areas are typically included, making it easy for guests to enjoy meals together. Onsite parking is another top amenity, ensuring that visitors have a straightforward experience when arriving by car.
When is the best time to visit Smithtown for a holiday rental?
The most popular time to visit Smithtown is during the peak season from May to July, when the area comes alive with vibrant activities and warm weather. This period is great for holiday rentals, as families and adventure seekers flock to enjoy the beautiful Long Island beaches and picturesque parks. Expect pleasant temperatures ranging from 20 to 30 degrees Celsius, ideal for outdoor activities, including hiking, biking, and watersports.July is the highlight of the season, offering a lively option with plenty of events, festivals, and opportunities to mingle with other travellers. You can explore charming local shops, indulge in fresh seafood, and take in the stunning coastal views while enjoying the summer sun.If you're looking for a more budget-friendly option, consider visiting in October. This month brings a unique charm as the summer crowds dissipate, allowing for a more relaxed experience. The fall foliage paints the landscape in beautiful hues, making it an excellent time for scenic walks and enjoying the region's natural beauty without the hustle and bustle.Ultimately, the best time to book a holiday rental in Smithtown will depend on whether you prefer the vibrant energy of the peak season or the tranquil beauty of autumn.
What are the top attractions in Smithtown?
In Smithtown, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local charm. The expansive Caleb Smith State Park Preserve offers scenic trails for hiking and nature walks, as well as opportunities for fishing and picnicking along the Nissequogue River. This park is a great spot for outdoor enthusiasts looking to explore the local flora and fauna.The Smithtown Historical Society provides insight into the town's rich history, featuring preserved sites such as the Frank Brush Barn and the Smithtown Museum. This area often hosts community events and educational programs, making it a lovely place to learn more about the town's heritage.For those interested in shopping and dining, the Main Street area offers a selection of quaint boutiques and eateries, great for a leisurely afternoon. Additionally, the nearby Long Island Aquarium in Riverhead is just a short drive away and presents a fantastic day out for families, showcasing marine life and interactive exhibits.
Are all fees included in the Smithtown holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Smithtown holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Smithtown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Smithtown holiday homes?
You can find great discounts on holiday homes in Smithtown on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Smithtown holiday home booking on Bookabach?
To find Smithtown holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Smithtown?
A long-stay holiday home in Smithtown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Smithtown holiday home?
Book your Smithtown holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Smithtown?
Prices for holiday homes in Smithtown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Smithtown to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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