Smithtown Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Smithtown vacation rentals

2 bedrooms, WiFi, bed sheets

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 ￥23,832
￥35,082 total
includes taxes & fees
Feb 16 - Feb 17
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Pool

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 ￥15,964
￥30,789 total
includes taxes & fees
Feb 16 - Feb 17
Tiny Home Private, Students, Nurses, Tech
Microwave, stovetop

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 ￥20,624
￥35,982 total
includes taxes & fees
Feb 20 - Feb 21
Lovely RV with AC in charming Bethpage a mile from the train to NYC
Classic Suite | Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (79 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
1 bedroom, iron/ironing board, free WiFi, bed sheets

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (7 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is ￥29,790
￥58,822 total
includes taxes & fees
Feb 16 - Feb 17
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Smart TV, books

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 ￥40,942
￥82,036 total
includes taxes & fees
Feb 16 - Feb 17
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
1 bedroom, free WiFi, bed sheets

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 ￥20,624
￥34,735 total
includes taxes & fees
Feb 20 - Feb 21
South Shore Studio in Mastic
Exterior

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)
"Perfect spot for a quick trip"
United States
James P.
The price is ￥18,980
￥27,795 total
includes taxes & fees
Feb 25 - Feb 26
Charming 1-bedroom apartment in fabulous Kings Park with WiFi, AC
1 bedroom, iron/ironing board, free WiFi, bed sheets

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)
"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 ￥15,812
￥25,921 total
includes taxes & fees
Feb 16 - Feb 17
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Terrace/patio

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Mastic
10.0 out of 10, Exceptional, (28 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is ￥79,532
￥183,833 total
includes taxes & fees
Feb 15 - Feb 16
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.
Fridge, microwave, oven, stovetop

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 ￥40,148
￥82,348 total
includes taxes & fees
Mar 11 - Mar 12
Modern Vacation home. Close to The Hamptons
Standard Room, 1 King Bed, Main Building | Property entrance

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 ￥47,714
￥54,872 total
includes taxes & fees
Feb 21 - Feb 22
Guesthouse at Norwalk Inn
Living area

The Moonrise Motel is a new vacation spot located in the heart of Kismet!

The Moonrise Motel is a new vacation spot located in the heart of Kismet!
Copiague
The price is ￥78,677
￥120,611 total
includes taxes & fees
Feb 16 - Feb 17
The Moonrise Motel is a new vacation spot located in the heart of Kismet!
Marina

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, (74 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 ￥31,471
￥71,737 total
includes taxes & fees
Feb 16 - Feb 17
Captain's Cottage - Cold Spring Harbor Water Views
1 bedroom, in-room safe, desk, free WiFi

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 ￥14,024
￥24,182 total
includes taxes & fees
Feb 20 - Feb 21
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Smart TV

THE OASIS @ LONG ISLAND

THE OASIS @ LONG ISLAND
Huntington Station
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
The price is ￥38,193
￥74,879 total
includes taxes & fees
Mar 11 - Mar 12
THE OASIS @ LONG ISLAND
Dining

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 ￥34,679
￥104,898 total
includes taxes & fees
Feb 24 - Feb 25
3 Story Beach Waterview, 3 KING bed, golf putting green!
Outdoor spa tub

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing

THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Commack
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful stay"
United States
Kenneth B.
The price is ￥64,921
￥104,718 total
includes taxes & fees
Feb 24 - Feb 25
THE GOOD VIBEZ HOUSE! Mini Golf Course,Heated Pool,Hot Tub,Game Room,Angel Wing
Interior

1-bedroom apartment with AC in Syosset

1-bedroom apartment with AC in Syosset
Syosset
The price is ￥21,999
￥67,017 total
includes taxes & fees
Feb 26 - Feb 27
1-bedroom apartment with AC in Syosset
Interior

2-bedroom apartment in delightful 4 minutes away from Babylon village

2-bedroom apartment in delightful 4 minutes away from Babylon village
West Babylon
The price is ￥24,443
￥41,717 total
includes taxes & fees
Feb 14 - Feb 15
2-bedroom apartment in delightful 4 minutes away from Babylon village
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

Viana Hotel and Spa, Trademark Collection by Wyndham

Viana Hotel and Spa, Trademark Collection by Wyndham

10/10 Excellent
"Everything was perfect! Liz helped with the check in process and she made our stay perfect! Would definitely recommend!!!! "
Tianna 1-night trip
Posted 2 days ago
Viana Hotel and Spa, Trademark Collection by Wyndham

Find out more about Smithtown

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Look no further and take a look at our great range of rental properties in Smithtown!

Frequently asked questions

Are there vacation rentals in Smithtown?

Yes, there are vacation rentals in Smithtown close to Blydenburgh County Park, or you can choose a more remote option if you're looking for extra privacy while you relax. Smithtown is known for its lake views.

What are some of the best vacation home rentals in Smithtown?

Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.: This vacation home rental outside of Smithtown is located by the ocean and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a pool table, and a hot tub so you can immerse yourself in your vacation.

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 larger area.

What are vacation rentals like in Smithtown?

Vacation rentals are private properties you can book for a couple days or more in Smithtown. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.