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Smithtown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Smithtown vacation rentals

A bedroom with a bed, pillows, a bedside table with a plant, and a wall-mounted air conditioner.

1. Rosemont by Tiny Away

Rosemont by Tiny Away
Verges Creek
10.0 out of 10, Exceptional, (1 review)
"Great two nights here exploring crescent head/south west rocks area. The house had everything we needed couldn’t be more perfect."
Australia
Amy B.
The price is CA $189
CA $239 total
includes taxes & fees
Oct 1 - Oct 2
Rosemont by Tiny Away
A clear blue beach with people swimming, a sandy shore, and a rocky coastline.

2. Billy Goat Cottage – Peaceful Country Escape Near Crescent Head

Billy Goat Cottage – Peaceful Country Escape Near Crescent Head
South Kempsey
9.4 out of 10, Exceptional, (3 reviews)
"lovely property"
Australia
Laura
The price is CA $250
CA $409 total
includes taxes & fees
Oct 13 - Oct 14
Billy Goat Cottage – Peaceful Country Escape Near Crescent Head
An aerial view of a coastal area with a sandy beach and dense forest.

3. Spoondrift - 5 Mins Walk to Beach

Spoondrift - 5 Mins Walk to Beach
South West Rocks
9.6 out of 10, Exceptional, (5 reviews)
"This is a great house, exactly as pictured, well set up, and situated close to a beach. SWR is a very sweet town with amazing beaches and a vibe perfect for relaxing and enjoying each other's company. "
United States
Sarah O.
The price is CA $1,041
CA $1,041 total
includes taxes & fees
Oct 14 - Oct 15
Spoondrift - 5 Mins Walk to Beach
A wooden cabin with a yellow door, two wooden chairs, and a bed visible through the door.

4. Yarriabinni Escape 2 by Tiny Away

Yarriabinni Escape 2 by Tiny Away
Stuarts Point
9.6 out of 10, Exceptional, (4 reviews)
"Friendly host. Beautiful space to stay"
Australia
Lindy T.
The price is CA $189
CA $239 total
includes taxes & fees
Oct 6 - Oct 7
Yarriabinni Escape 2 by Tiny Away
A narrow hallway with teal and white striped walls, a wooden door, and a sink area with a mirror and hanging lights.

5. 'Alice' Crescent Head's coolest retro caravan

'Alice' Crescent Head's coolest retro caravan
Crescent Head
9.2 out of 10, Wonderful, (11 reviews)
"Amenities good. Nice peaceful place."
Australia
jennifer l.
The price is CA $219
CA $330 total
includes taxes & fees
Oct 1 - Oct 2
'Alice' Crescent Head's coolest retro caravan
A modern kitchen with white cabinets, a wooden countertop, a built-in stove, and a window with blinds.

6. Beach Shack 7 - Escape to the Coastal Chic Apartment

Beach Shack 7 - Escape to the Coastal Chic Apartment
Crescent Head
8.8 out of 10, Excellent, (14 reviews)
"The unit was clean and had everything needed; appreciated face washers and hairdryer; easy walk to the beach"
Australia
Christine M.
The price is CA $385
CA $385 total
includes taxes & fees
Oct 13 - Oct 14
Beach Shack 7 - Escape to the Coastal Chic Apartment
A bedroom with a bed, bedside table, lamp, and a view of palm trees through the window.

7. Beach Shack 6 your ideal retreat just moments from the beach!

Beach Shack 6 your ideal retreat just moments from the beach!
Crescent Head
10.0 out of 10, Exceptional, (1 review)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Awesome residence,fab location,wifey and i cant recommend it higher enough"
United States
Mick V.
The price is CA $385
CA $385 total
includes taxes & fees
Oct 13 - Oct 14
Beach Shack 6 your ideal retreat just moments from the beach!
A modern kitchen with white cabinets, a microwave, and a stove. There is a ceiling fan and a window with a view of greenery outside.

8. Beach Shack 5

Beach Shack 5
Crescent Head
7.6 out of 10, Good, (8 reviews)
"Rating Details: The property manager was more than helpful. The vacation rental was very clean. I was more than happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: A perfectly cosy well appointed space in beautiful Crescent Head easy walking distance to everything you want.Sounds like improvements have been made since some past reviews as the accommodation had both a ceiling fan and a...
United States
Andrew D.
The price is CA $385
CA $385 total
includes taxes & fees
Oct 13 - Oct 14
Beach Shack 5
A modern living room with a sectional sofa, a ceiling fan, and large sliding glass doors leading to an outdoor area.

9. Luxe Coastal Escape. Walk to beach, cafe and shops.

Luxe Coastal Escape. Walk to beach, cafe and shops.
Crescent Head
10.0 out of 10, Exceptional, (1 review)
The price is CA $430
CA $718 total
includes taxes & fees
Oct 6 - Oct 7
Luxe Coastal Escape. Walk to beach, cafe and shops.
A small cabin with a deck, surrounded by trees and grass.

10. Yarriabinni Escape 1 by Tiny Away

Yarriabinni Escape 1 by Tiny Away
Stuarts Point
8.0 out of 10, Very good, (1 review)
"It was very clean. In a great location. I enjoyed my stay there."
Australia
Kim S.
The price is CA $189
CA $239 total
includes taxes & fees
Oct 5 - Oct 6
Yarriabinni Escape 1 by Tiny Away
A kitchen with white cabinets, a stove, a sink, and a window with a view of the outside.

11. Beach Shack 8 - Coastal Villa Steps from Beach & Village

Beach Shack 8 - Coastal Villa Steps from Beach & Village
CRESCENT HEAD
The price is CA $385
CA $385 total
includes taxes & fees
Oct 19 - Oct 20
Beach Shack 8 - Coastal Villa Steps from Beach & 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

Costa Rica Motel

Costa Rica Motel

8/10 Good
"Very basic but comfortable accomodation. Great bathroom and water pressure. Room was a bit dark. Aircon and mini fridge were good and so was parking. My room was missing coffee cups and I was provided one upon request. There was a strange wet stain in the foot of my bed as if someone’s spilt something. Overall good for a brief stay. Conveniently located and close to the shops."
Anna 3-night trip
Posted 1 day ago
Costa Rica Motel

Find out more about Smithtown

Everything you need to know about Smithtown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Smithtown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Smithtown vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Smithtown vacation rentals we have selected for you start as low as CA $409 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 vacation 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 vacation.

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 vacation rentals in Smithtown?

Yes, there are vacation rentals close to popular attractions in Smithtown, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Smithtown?

Crescent Head Beach House: This vacation home near Smithtown offers a balcony, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

What can I see and do in Smithtown?

While you're exploring the area, Riverside Park and Hat Head National Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Hat Head Beach and Smoky Cape Lighthouse.

What are vacation rentals like in Smithtown?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Smithtown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for family trips.