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Smithtown Vacation Rentals

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Sep 28 - Sep 29
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Vacation Rentals in Smithtown

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
Private kitchen

Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown

5.0 out of 10, (2)
"Overall clean space and super easy check in/out. Location is on a quiet street/neighborhood which is nice. Not full a/c in rooms but had two floor fans; was hot in summertime but manageable for a short stay. Had a nice deadbolt on door to lock it. Awkward entrance as you go through the back of the house and all the way around the property, but it isn't terrible. A bit of a dead zone for Verizon but T-mobile was OK; Wi-Fi was available which was needed. Good for easy overnight stay and cheaper...
The price is ￥23,320
￥34,328 total
includes taxes & fees
Sep 30 - Oct 1
Spacious 2-bedroom apartment with WiFi, AC in wonderful Hauppauge/ Smithtown
DUNE Fairfield Beach
Private beach nearby, sun loungers, beach umbrellas, beach towels

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (71)
"Incredible staff, friendly, helpful. "
DUNE Fairfield Beach
Guesthouse at Norwalk Inn
Standard Room, 1 King Bed, Main Building | Property entrance

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very Good, (39)
"it was amazing will stay again food was good comfort was great "
The price is ￥37,196
￥42,776 total
includes taxes & fees
Oct 7 - Oct 8
Guesthouse at Norwalk Inn
Spacious Home Located Close to Stony Brook!
Property grounds

Spacious Home Located Close to Stony Brook!

7.0 out of 10, Good, (20)
"Great stay great people great costumer care definitely reccomend"
The price is ￥46,955
￥105,226 total
includes taxes & fees
Oct 10 - Oct 11
Spacious Home Located Close to Stony Brook!
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Beach

“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.

10.0 out of 10, Exceptional, (2)
"Friendly host, very good location and a simple check-in process. Few minutes drive to the beach. "
The price is ￥35,653
￥49,445 total
includes taxes & fees
Oct 6 - Oct 7
“THE GOOSE” A Charming 2-bedroom bungalow with WiFi and AC in Mastic Beach.
Newly Renovated Luxury Beach House Ocean Bay Park
Outdoor dining

Newly Renovated Luxury Beach House Ocean Bay Park

10.0 out of 10, Exceptional, (71)
"Very nice place for a family to stay"
The price is ￥94,044
￥175,420 total
includes taxes & fees
Sep 29 - Sep 30
Newly Renovated Luxury Beach House Ocean Bay Park
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bedroom, iron/ironing board, free WiFi, bed sheets

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

9.4 out of 10, Exceptional, (29)
"its small but very nice for a short stay would recommend."
The price is ￥14,800
￥24,598 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR
Dining

Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR

9.0 out of 10, Wonderful, (16)
"The property was very quaint and comfortable. We'll probably stay again in the future"
The price is ￥12,333
￥22,409 total
includes taxes & fees
Oct 3 - Oct 4
Private Queen BedRm Pet Pally, Work, Events, LTR, MTR, STR
Tiny Home Private, Students, Nurses, Tech
Property grounds

Tiny Home Private, Students, Nurses, Tech

9.0 out of 10, Wonderful, (4)
"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!"
The price is ￥15,622
￥30,297 total
includes taxes & fees
Sep 29 - Sep 30
Tiny Home Private, Students, Nurses, Tech
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC
Terrace/patio

Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC

8.8 out of 10, Excellent, (8)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
Waterfront Beach Cottage Sunsets Inspiring Cozy Peaceful Private 1 hr NYC
Charming 3-bedroom modern family retreat!
Property grounds

Charming 3-bedroom modern family retreat!

9.0 out of 10, Wonderful, (4)
"Spacious, clean and host was very responsive to any questions we had ! "
The price is ￥49,780
￥74,811 total
includes taxes & fees
Sep 29 - Sep 30
Charming 3-bedroom modern family retreat!
Walk to Beach 2BR Near Dining & Shopping
Property grounds

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (20)
"The beach is private and you need to be a Brookhaven resident to be admitted. This is not specified anywhere on the listing. Communication about this with the owner via app was rather poor. "
The price is ￥16,818
￥41,249 total
includes taxes & fees
Sep 29 - Sep 30
Walk to Beach 2BR Near Dining & Shopping
1 bed room basement apartment.
Microwave, stovetop

1 bed room basement apartment.

8.2 out of 10, Very Good, (10)
"The property was very spacious and can bring family there. "
The price is ￥14,949
￥25,032 total
includes taxes & fees
Oct 6 - Oct 7
1 bed room basement apartment.
1 bedroom 1 bath private entrance
Interior

1 bedroom 1 bath private entrance

8.8 out of 10, Excellent, (20)
"Augustine was very helpful and nice!It was a great price that enabled us to visit friends and family for the holidays "
The price is ￥17,490
￥29,717 total
includes taxes & fees
Oct 1 - Oct 2
1 bedroom 1 bath private entrance
Modern Vacation home. Close to The Hamptons
Fridge, microwave, oven, stovetop

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is ￥49,705
￥94,193 total
includes taxes & fees
Sep 30 - Oct 1
Modern Vacation home. Close to The Hamptons
Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park
Beach

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park

Spacious 5-bedroom house, sleeps 11 with AC, WiFi in adorable Ocean Bay Park
Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow
Property grounds

Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow

9.0 out of 10, Wonderful, (10)
"Perfect location to enjoy Northport! Everything is within walking distance. Host was very helpful and accommodating. Great stay and will definitely return! "
The price is ￥79,917
￥141,517 total
includes taxes & fees
Sep 30 - Oct 1
Waterfront Beautiful Fun Beach House Sunsets Inspiring Peaceful 1hr NYC Wow
Luxury and Affordable Family Home
Interior

Luxury and Affordable Family Home

7.4 out of 10, Good, (8)
"My family and I had the pleasure of staying here during the Christmas holidays, and it was an excellent experience. We were especially grateful for the accessibility features, as my grandmother (85 years young), who uses a walker and had recently undergone surgery, was able to comfortably stay on the main floor. The property had just a few steps to enter, and best of all, there was a bedroom and full bathroom on the main level, along with ample room for a walker or wheelchair.The home itself was...
The price is ￥68,616
￥141,415 total
includes taxes & fees
Sep 29 - Sep 30
Luxury and Affordable Family Home
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!
Fridge, microwave, oven, stovetop

OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!

9.0 out of 10, Wonderful, (53)
"Has a very nice stay."
OCEAN BEACH, Fire Island, 3 bedroom, close to ferry, village and all beaches!
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Marina

Adorable Cottage with Water Views, Across the street from Prime & other eateries

9.8 out of 10, Exceptional, (67)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries
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

East Norwich Inn

East Norwich Inn

10/10 Excellent
"Clean, quiet, with a friendly staff that is always ready to assist. House keeping is great. Wish there was a breakfast and wish the gym was not so isolated in the basement. "
Anne 2-night trip
Posted 14 hours ago
East Norwich Inn

Find out more about Smithtown

Find out more about Smithtown

Search for holiday rentals in Smithtown on Expedia! You can easily find your home rentals, villas, holiday apartments in Smithtown using one of the methods below:

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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 Home Located Close to Stony Brook!: This vacation home rental outside of Smithtown offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Smithtown?

Family-friendly attractions include Blydenburgh County Park, whereas Nissequogue River is a spot to enjoy the outdoors. Stonebridge Golf Links and Country Club and Caleb Smith State Park are other places to visit while you're in town.

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.