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Vacation rentals in Smithtown

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Top-rated vacation rentals in Smithtown

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Rental unit in Port Jefferson Station

4.96 out of 5 average rating, 171 reviews

All Private Bright Spacious Close to All

DISINFECTED AND CLEANED BEFORE YOU ARRIVE! Spacious ground level PRIVATE apt with lots of natural light. Full kitchen/new stove/fridge/Keurig.Bedrm- queen sz bed, living rm -queen sz sofa sleeper. Also available is queen air mattress w/ topper. Washer/Dryer. Minutes away to the Port Jeff Village shops&restaurants/Ferry/LIRR, hospitals, & Stony Brook. Small beaches 10-15min drive, large beaches,Shop Outlets & Wineries 25 -60 minute. PLEASE NOTE: Extra $2 Daily Fee for charging electric car.

Rental unit in Huntington

4.95 out of 5 average rating, 261 reviews

Historic Huntington Village Private Retreat

50 min from NYC on LIRR to Huntington. Less than one mile from the train station and an easy walk to Huntington village in an historic, vibrant, relaxed and unique neighborhood. Plenty to do in the area with many parks and beaches and a great place to enjoy nature. It is a short walk (a half mile) to Huntington village where there are many great restaurants, bars, and shops, plus the Paramount Theater. This stylish comfortable place is clean, cozy and quiet. Sorry, no pets allowed, dander-free!

Rental unit in Smithtown

4.98 out of 5 average rating, 190 reviews

Mimi's Retreat -Private street level basement apt.

Walk-in street level one bedroom basement apartment with keypad entry in a quiet, safe neighborhood. Fully equipped kitchen includes cooking essentials, microwave, air fryer, electric tea kettle, Keurig coffee machine and toaster. Premium cable TV, excellent 5G Wi-Fi and Smart TV. Free parking on premise. Outside Security Camera's. Within walking distance to LIRR, restaurants and shopping. Centrally located between NYC, LI beaches & North Fork wine country. *NO PETS and NO SMOKING +

Rental unit in Port Jefferson Station

4.93 out of 5 average rating, 188 reviews

Brand New Modern Spacious Apartment

Brand new private 1 BASEMENT bedroom apartment fully furnished. Just bough a brand new comfortable Queen size bed. Full kitchen, bathroom, living room. Bedroom has walk in closet. Apartment is in the BASEMENT of a 2500 sft home. The apartment is at least 800 square feet and has a private entrance. Has Keurig ( which I supply coffee , sugar and creamer for) , full stove, big frig, a microwave, toaster, hair Dryer and iron. Plenty of towels, shampoo, conditioner and soap. NO PETS ALLOWED

Home in Stony Brook

5 out of 5 average rating, 101 reviews

Cottage in the heart of Stony Brook Village

Totally renovated 100 year old charming but modern cottage steps from the Three Village Inn, Country House Restaurant, Stony Brook Village, Jazz Club, Sand St. Beach, Avalon Park, Carriage museum and the Long Island Music & Entertainment Hall of Fame. You will have the private upper floor of the cottage with a private entrance. There is a spacious porch and front yard with lounge chairs where you can watch the deer, chipmunks, birds, & rabbits. Short ride to Stony Brook University.

Guest suite in Stony Brook

4.79 out of 5 average rating, 600 reviews

Studio in Stony Brook

We have contactless check-in procedure & fully private entrance. Please contact with any questions! Large clean studio space that is totally private from the main residence. Private bathroom with toiletries included. Close to beaches, shopping, and SUNY hospital and campus by car or bus. Pull-out loveseat with twin size mattress available for an extra charge. (Book for “3 Guests” for this regardless of occupancy so we know to prepare the bed.)

Guest suite in Stony Brook

4.94 out of 5 average rating, 131 reviews

Cozy cottage in a charming historic village!

Our guest suite is perfectly located in the Old Historic District of Stony Brook Village across from the duck pond. We are only a few steps away from Avalon Park and Preserve, Sand Street Beach, the Long Island Museum, restaurants and shops. The village offers numerous places to explore in our quaint town and even more day trips on the outskirts where you can enjoy the simple pleasures during your time at our relaxing cottage.

Rental unit in Northport

4.85 out of 5 average rating, 170 reviews

Harbor Studio - Across from historic Northport doc

Across the street from historic Northport dock and the beautiful town park, this downtown studio is walking distance to everything. Drive or boat in to town and have a lovely convenient place to stay close to everything. Dining, shopping, the park, and the Famous Engleman theater. The studio has a private entrance, full kitchen, and bath with shower and tub. Enjoy a night, weekend, or whole week in historic Northport Village.

Cottage in Kings Park

4.79 out of 5 average rating, 164 reviews

Cozy Riverside Cottage

This is a private cottage on its own lot with its own driveway and yard located in a quiet residential neighborhood. Several grocery stores and restaurants for delivery/pick up in the area. 400 MBPS Internet connection for those who need a reliable internet connection for work/movie streaming! Please note guest maximum is 4. There are no additional guests or visitors allowed.

Rental unit in Islip Terrace

4.88 out of 5 average rating, 188 reviews

PHILS COZY Private studio(new kitchen/fresh paint)

My place is close to restaurants and dining, the beach, and family-friendly activities. You’ll love my place because of light, comfy bed, the kitchen, the coziness, and the high ceilings and privacy. Good for couples, solo, business travelers, and furry friends (pets). Located near the airport and train station. I ESPECIALLY PREFER MONTHLY OR SEASONAL LENGTHY VISITORS.

Home in Ronkonkoma

4.86 out of 5 average rating, 163 reviews

Convenient home in Ronkonkoma

Charming cape that is completely private. This is not an apartment within a house. The entire home and yard are yours to enjoy with complete privacy. Conveniently located 6 blocks from LIRR Ronkonkoma Station, 2 miles from Islip MacArthur Airport, and 1 mile from Long Island Expressway. 5.5% Occupancy Tax included.

Guest suite in Lake Ronkonkoma

4.99 out of 5 average rating, 258 reviews

Private New Apartment

Open concept living. Cathedral ceilings. 1 Bedroom, Full Bath. Private parking. Patio. 5 minutes from train, 15 minutes to MacArthur Airport. Close to Stony Brook, South shore ocean beaches, and the north shore of Long Island. Perfect if you are planning on heading out east to the wineries!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Smithtown vacation rentals

Free parking on premises

Air conditioning

Stay near Smithtown's top sights

Stop & Shop8 locals recommend

Caleb Smith State Park7 locals recommend

Mannino's7 locals recommend

Uncle Giuseppe's Marketplace7 locals recommend

Whisper Vineyards7 locals recommend

Maureen's Kitchen6 locals recommend

Other great vacation rentals in Smithtown

Guest suite in West Islip

4.93 out of 5 average rating, 27 reviews

NEWLY RENOVATED 1 BEDROOM APT W/ HEATED POOL

Rental unit in Central Islip

5 out of 5 average rating, 38 reviews

Cozy studio w/ private entrance

Rental unit in Ronkonkoma

4.89 out of 5 average rating, 44 reviews

Casa La-Detente Thanksgiving. Christmas, New Year

Rental unit in Smithtown

4.86 out of 5 average rating, 29 reviews

Paradise on Long Island

Rental unit in Huntington Station

4.89 out of 5 average rating, 99 reviews

Clean Cozy Studio with Private Entrance.

Guesthouse in Bay Shore

4.89 out of 5 average rating, 19 reviews

Cozy Place

Rental unit in Port Jefferson Station

4.84 out of 5 average rating, 70 reviews

The Elite Enclave

Place to stay in Coram

4.99 out of 5 average rating, 91 reviews

T&T Unique Space

Quick stats about vacation rentals in Smithtown

Total rentals
40 properties
Total number of reviews
2.4K reviews
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool

Frequently Asked Questions

Do apartment rentals in Smithtown have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Smithtown. Enjoy a tailored experience with all the comforts you desire.
Are there Smithtown vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Smithtown, available on Airbnb. Make a splash and soak up the sun in style!
Are there vacation rentals with a dedicated workspace in Smithtown?
Yes! Work meets play with ease at over 20 vacation rentals in Smithtown featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Smithtown have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Smithtown. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Smithtown?
Experience the best of Smithtown with our apartment rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Smithtown have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Smithtown. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Smithtown have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Smithtown. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Smithtown?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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