Holiday rentals in Smithtown

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Top-rated holiday rentals in Smithtown

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Guest favourite

Flat in Port Jefferson Station

4.97 out of 5 average rating, 144 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.

4–11 Dec

£130 per night

Guest favourite

Flat in Huntington

4.97 out of 5 average rating, 219 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!

18–25 Nov

£116 per night

Guest favourite

Flat in Stony Brook

4.99 out of 5 average rating, 129 reviews

Home Away From Home To SBU & SB Hospital

Stay in our private studio apartment that has the vibe of warmth and serenity. It is situated in a quiet neighborhood of Stony Brook with beautiful tree-lined streets. The studio has a warm and rustic feel and detailed amenities to make your visit a pleasure. It is perfect for someone traveling for business at Stony Brook Hospital or for parents or grandparents of a student attending Stony Brook University (5 minutes). It is great for couples attending a wedding at the Harbor or nearby towns.

12–19 Jan

£117 per night

Guest favourite

Flat in Deer Park

4.97 out of 5 average rating, 112 reviews

Best Studio-Private Entrance+Parking-Close To All

Make yourself at home! This Deer Park Den is your perfect suburban hideaway in the heart of Long Island, close to everything and right in the middle of all the fun. Walking distance to lots of great restaurants that give you plenty of great options for ordering in or dining out. Other local destinations include: - Tanger outlets (1 Mile) - Heartland Golf Park (1.5 Miles) - Edgewood Oak Brush Plains Preserve (0.5 Mile) - Robert Moses state park (12 Miles) - Sunken Meadow state park (12 miles)

25 Oct – 1 Nov

£111 per night

Guest favourite

Flat in Smithtown

4.98 out of 5 average rating, 183 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 +

30 Nov – 7 Dec

£146 per night

Guest favourite

Home in Holbrook

4.91 out of 5 average rating, 237 reviews

Cozy studio

We are 10 minutes away to MacArthur Airport in Islip, 5 minutes to shopping center where you can find supermarkets, restaurants, and stores. We are 10 minutes away from LIRR train station where you can get a ride to Manhattan. Although the studio is centrally located a car or Uber is recommended,. You'll have your own bathroom, kitchen with microwave, coffee maker, toaster, fridge, air conditioner, tv with cable and internet. Our study is a FREE SMOKING PLACE! Not smoking or vaping!

12–19 Jul

£90 per night

Guest favourite

Flat in Stony Brook

4.78 out of 5 average rating, 544 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.)

1–8 Oct

£121 per night

Guest favourite

Guest suite in Stony Brook

4.95 out of 5 average rating, 110 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.

27 Sept – 4 Oct

£166 per night

Guest favourite

Flat in Northport

4.92 out of 5 average rating, 129 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.

23–30 Oct

£113 per night

Guest favourite

Cottage in Patchogue

4.95 out of 5 average rating, 202 reviews

Quaint Cottage on Long Island's South Shore.

The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

3–10 May

£131 per night

Guest favourite

Home in Ronkonkoma

4.86 out of 5 average rating, 147 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.

4–11 Jul

£105 per night

Guest favourite

Flat in Brentwood

4.89 out of 5 average rating, 231 reviews

Eco-friendly studio with Private entrance

We have created this quaint space with our guest in mind in order to keep it simple at this peaceful and centrally-located place. Studio apartment with your own entrance, kitchen , bathroom and work area. All the amenities of a super host.

1–8 Jan

£86 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Smithtown holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Smithtown's top sights

Maureen's Kitchen6 locals recommend

Insignia Prime Steak & Sushi4 locals recommend

Blydenburgh County Park5 locals recommend

Cafe Havana3 locals recommend

Uncle Giuseppe's Marketplace7 locals recommend

Sangria 715 locals recommend

Other great holiday rentals in Smithtown

Guest favourite

Flat in Islip Terrace

4.99 out of 5 average rating, 138 reviews

Near all! - Full Kitchen, Backyard & Fire Pit!

19–26 Nov

£147 per night

Guest favourite

Guest suite in Smithtown

4.93 out of 5 average rating, 42 reviews

Bright 1-Bdrm Studio Apt on Quiet Tree-Lined St.

3–10 Jun

£125 per night

Guest favourite

Guest suite in Kings Park

4.94 out of 5 average rating, 53 reviews

*NEW LUX Northshore River KING, privacy deck/yard

16–23 Jan

£131 per night

Superhost

Home in Hauppauge

4.86 out of 5 average rating, 14 reviews

Teal oasis private guest house

15–22 Dec

£88 per night

Guest favourite

Home in Ronkonkoma

4.9 out of 5 average rating, 29 reviews

The Ronkonkoma Bungalow

10–17 Sept

£134 per night

Guest favourite

Campervan/Motorhome in Brentwood

5.0 out of 5 average rating, 18 reviews

The Relaxing RV #3

7–14 May

£79 per night

Guest favourite

Flat in Centereach

4.93 out of 5 average rating, 15 reviews

Stony Brook Sanctuary: Hideaway near the Hospital

18–25 Jun

£97 per night

Guest favourite

Flat in Smithtown

4.88 out of 5 average rating, 16 reviews

Paradise on Long Island

14–21 Nov

£145 per night

Show all

Quick stats about holiday rentals in Smithtown

Total rentals
40 properties
Local attractions
Watermill Caterers, Maureen's Kitchen and Insignia Prime Steak & Sushi
Popular amenities
Kitchen, Wifi and Pool
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Total number of reviews
2K reviews

Holiday rentals in Smithtown

Top-rated holiday rentals in Smithtown

Flat in Port Jefferson Station

Flat in Huntington

Flat in Stony Brook

Flat in Deer Park

Flat in Smithtown

Home in Holbrook

Flat in Stony Brook

Guest suite in Stony Brook

Flat in Northport

Cottage in Patchogue

Home in Ronkonkoma

Flat in Brentwood

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Smithtown holiday rentals

Stay near Smithtown's top sights

Other great holiday rentals in Smithtown

Flat in Islip Terrace

Guest suite in Smithtown

Guest suite in Kings Park

Home in Hauppauge

Home in Ronkonkoma

Campervan/Motorhome in Brentwood

Flat in Centereach

Flat in Smithtown

Quick stats about holiday rentals in Smithtown

Total rentals

Local attractions

Popular amenities

Wifi availability

Rentals with dedicated workspaces

Total number of reviews

Destinations to explore