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Smithtown Vacation Rentals

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Vacation Rentals in Smithtown

DUNE Fairfield Beach
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach
3.0 star property
10.0 out of 10, Exceptional, (10)
"Modern cottage near the beach. Clean and comfortable. Very responsive."
The price is ￥30,420
per night
Jun 6 - Jun 7
DUNE Fairfield Beach
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
Interior
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
8.8 out of 10, Excellent, (13)
"4 families came from CA for a graduation celebration. Enough room and beds for all 10 of us. Easy access to lake. Backyard is huge, had fun playing badminton and volleyball. Also lit a fire at the fire pit one night. Managers were very responsive to our questions and requests There is a projector and we were able to watch movies at night. Pretty cool. Had a great stay."
The price is ￥124,936
per night
Jun 5 - Jun 6
Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres
The President's Mansion Stunning 7-Bedroom 4 Bath
Interior
The President's Mansion Stunning 7-Bedroom 4 Bath
10.0 out of 10, Exceptional, (1)
"This is a huge house and brand new kitchen and living room and spacious bathrooms and guest rooms. We love and enjoyed it, our kids and parents were very excited to come and spend time together, we appreciate the opportunity to stay together! BTW, it was nice price to compare others!"
The President's Mansion Stunning 7-Bedroom 4 Bath
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Dog-friendly home just blocks from the bay with deck & private hot tub
Property grounds
Dog-friendly home just blocks from the bay with deck & private hot tub
8.4 out of 10, Very Good, (17)
"The house was clean. Communication with management company was subpar. We got scripted responses to all questions, and false information. For example, we asked if hot tub was working and was told it was. When we arrived, the hot tub was broken and dirty. Also, check-out is at 10am and there is nowhere to leave belongings if you’d like to stay in FI for the day. They should allow a place to keep luggage prior to departure. Overall, great and clean house and amazing location!"
Dog-friendly home just blocks from the bay with deck & private hot tub
Beachfront Romance: Rustic Home w/ Private Beach
On the beach
Beachfront Romance: Rustic Home w/ Private Beach
9.2 out of 10, Wonderful, (39)
"The house is small but it has everything you need. The ocean was lovely to watch and good scavenging for rocks and sea glass. Very private place. My pup and I had a good time!"
Beachfront Romance: Rustic Home w/ Private Beach
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
Fridge, microwave, oven, stovetop
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
8.0 out of 10, Very Good, (38)
"The property was misrepresented and unsafe. My parents didnt stay with us due to conditions of the property. We contacted Vacasa the rental management company and decided to leave the property and stay with friends as the windows were broken and shattered and the master bed was broken, no wifi, no functional washer and the list goes on. I expect a full refund from VRBO....I am a frequent client of VRBO and this was not acceptable. Please advise how to go about obtaining a full refund or I will...
Spacious Dog-Friendly Home with Renovated Kitchen and Bathrooms
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly
Interior
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly
8.4 out of 10, Very Good, (5)
"We found the house to be really cute and fun to stay in. The location was excellent and we even saw a deer on our last morning! Our main issues, and why this isn’t a 5 star rating, were that multiple lighting fixtures weren’t working and there was an entire bed missing. The ad mentions “1 queen, 1 double, 4 twin’ beds however there’s really 1 queen and 4 twins. This could have caused a big problem if our group was just a bit larger. The ad should be changed to reflect the accurate information...
Charming home close to beach with fast WiFi & washer/dryer - dog-friendly
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
1 bedroom, iron/ironing board, WiFi, bed sheets
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
9.4 out of 10, Exceptional, (9)
"It’s was perfect for what I needed. A comfortable place to sleep and a hot shower. The room was perfectly appointed also. I would recommend and stay there again. "
The price is ￥14,836
per night
Jun 10 - Jun 11
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Waterfront Home magnificent view!
Property grounds
Waterfront Home magnificent view!
9.4 out of 10, Exceptional, (94)
"Our second stay here was just as great as the first. Very comfortable and quiet. Mike is a great host. Look forward to our next visit."
The price is ￥19,521
per night
Jun 5 - Jun 6
Waterfront Home magnificent view!
1 bedroom 1 bath private entrance
1 bedroom, WiFi, bed sheets
1 bedroom 1 bath private entrance
9.6 out of 10, Exceptional, (8)
"Neat, clean & quite"
The price is ￥20,302
per night
Jun 5 - Jun 6
1 bedroom 1 bath private entrance
💎 Modern Chic Getaway, Biz Friendly, Close 2 all 👣
1 bedroom, in-room safe, desk, iron/ironing board
💎 Modern Chic Getaway, Biz Friendly, Close 2 all 👣
💎 Modern Chic Getaway, Biz Friendly, Close 2 all 👣
Waterfront Cottage cute and cozy
TV
Waterfront Cottage cute and cozy
9.6 out of 10, Exceptional, (74)
"Cute cottage, very clean! Right on the canal complete with little beach, firepit, outdoor grill, lounge chairs, etc. Cottage was comfortable, well maintained. Nice little touches everywhere. Quiet area, great for relaxation! Would definitely go back!!!"
The price is ￥17,179
per night
Jun 5 - Jun 6
Waterfront Cottage cute and cozy
2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment
Fridge, microwave, oven, stovetop
2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment
8.6 out of 10, Excellent, (21)
"We had a great time the property looked like the picture minor hiccups"
2 Bedroom Apt. in Ocean Bay Park, walk to beach and entertainment
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
8.6 out of 10, Excellent, (8)
"The property was clean and large and the outdoor space made for a fun gathering place, especially for the children in our group. It would have been nice to have dedicated spaces to hang towels and clothes, especially as we had so many people staying. The hosts were friendly and accommodating and we would stay again."
20 Minutes from the Hamptons! Quiet 4 bedroom getaway with pool.
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Interior
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
10.0 out of 10, Exceptional, (1)
"Great location and great house. Didn't understand why we couldn't flush toilet paper in master bathroom. Otherwise everything was great."
The price is ￥46,851
per night
Jun 5 - Jun 6
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome
Interior
Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome
6.2 out of 10, (14)
"We all had an amazing time. Convenience to the beach was a bonus. Spectacular views of the ocean n the bay. Plenty of space , screen doors were annoying ( but I also live on the beach and understand how beat up everything gets). Would definitely rent this house again."
Large Home with Ocean Views, Fireplace, and Gas Grill - Dogs Welcome
3 Story Beach Waterview, 3 KING bed, golf putting green!
Interior
3 Story Beach Waterview, 3 KING bed, golf putting green!
10.0 out of 10, Exceptional, (8)
"My family and I, rented this beautiful BNB to stay in while in town for my Grandmothers 90th Birthday. The home was exactly as pictured on the site, it was by far the cleanest and best taken care property that we have rented through VRBO! We were beyond impressed by the Host Eddie and his home! We willlllll be back!"
The price is ￥33,264
per night
Jun 11 - Jun 12
3 Story Beach Waterview, 3 KING bed, golf putting green!
Designer beach cottage & studio with bikes, outdoor shower, deck - walk to beach
Fridge, microwave, oven, stovetop
Designer beach cottage & studio with bikes, outdoor shower, deck - walk to beach
9.4 out of 10, Exceptional, (16)
"We enjoyed our stay. The house was set up perfectly for two families traveling together. The beds were comfy and we loved the outdoor showers. There were only two bikes for 9 of us so we ended up renting. There were also not enough beach chairs and some were not in great shape. The fridge in the kitchen needed to be replaced and there were not enough coffee cups and dishes."
Designer beach cottage & studio with bikes, outdoor shower, deck - walk to beach
Private 1 bedroom apt in a quiet neighborhood, close to all!
Fridge, microwave, oven, stovetop
Private 1 bedroom apt in a quiet neighborhood, close to all!
9.4 out of 10, Exceptional, (11)
"Thank you very much for being so accommodating with our stay! It was very clean, had all the essentials plus extra and we really liked how we had our own private patio. Will definitely be staying again in the future!"
The price is ￥22,176
per night
Jun 10 - Jun 11
Private 1 bedroom apt in a quiet neighborhood, close to all!
Charming Cape Close to the Ocean
Property grounds
Charming Cape Close to the Ocean
5.2 out of 10, (5)
"Great area and good rental"
Charming Cape Close to the Ocean
Don't see what you're looking for?
See all available properties in Smithtown
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.

Other types of properties in Smithtown you may be interested in

Radisson Hotel Hauppauge-Long Island
Breakfast served, American cuisine
Radisson Hotel Hauppauge-Long Island
3.5 star property
6.0 out of 10, (1007)
"Should have a free breakfast for the price they charged. "
The price is ￥18,451
per night
Jun 23 - Jun 24
Radisson Hotel Hauppauge-Long Island
East Norwich Inn
Exterior
East Norwich Inn
2.5 star property
7.8 out of 10, Good, (1735)
"Quiet location and facility in a great area with lots of places to dine. Chase and TD within walking distance. Staff works hard to keep place clean."
The price is ￥16,865
per night
Jun 6 - Jun 7
East Norwich Inn
Inn at Jericho
Standard Room, 1 Queen Bed, Accessible | 1 bedroom, premium bedding, desk, laptop workspace
Inn at Jericho
2.0 star property
7.8 out of 10, Good, (1001)
"everything clean, I like the hotel"
The price is ￥15,350
per night
Jun 19 - Jun 20
Inn at Jericho
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.

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?

Private Lake house with cable!! Treehouse, kayaks, fishing and quads. 1.3 Acres : This vacation home rental outside of Smithtown is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 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.

Recent reviews of Smithtown properties
Expedia verified reviews

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

5/5 Excellent
Charming historical hotel
"My family had a very comfortable stay at this historical hotel. We stayed at a suite in their guest house and it was the perfect room for families. Not much is in walking distance but everything is close by if you have a car. Their rates are very competitive and a great value for the price. I would bring my family here again for sure. "
A verified traveler stayed at Norwalk Inn & Conference Center
Posted 10 hours ago
Norwalk Inn & Conference Center