A rocky beach with large boulders and a clear view of the ocean.

Smithtown Vacation Rentals

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Our top choices for Smithtown vacation rentals

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (96 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is AED 748
AED 1,085 total
includes taxes & fees
14 Jul - 15 Jul
DUNE Fairfield Beach

Charming Rocky Point Home ~ 1 Mi to Beach!

Charming Rocky Point Home ~ 1 Mi to Beach!
3.0 star property
Rocky Point
The price is AED 1,308
AED 2,264 total
includes taxes & fees
19 Jul - 20 Jul
Charming Rocky Point Home ~ 1 Mi to Beach!

Sundown Escape-South Shore Long Island

Sundown Escape-South Shore Long Island
2.0 star property
Bay Shore
10.0 out of 10, Exceptional, (1 review)
"Very clean. Easy to get to. Listing as described. Bed and furniture are nice and comfy. Only thing I would add is a broom and dust pain and some Clorox wipes so guest can keep it neat. 5 stars! Very nice host. "
United States
Samantha
The price is AED 472
AED 1,085 total
includes taxes & fees
8 Jul - 9 Jul
Sundown Escape-South Shore Long Island

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, (80 reviews)
"A true port in the storm"
United States
Trey S.
The price is AED 1,396
AED 2,589 total
includes taxes & fees
7 Jul - 8 Jul
Captain's Cottage - Cold Spring Harbor Water Views

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is AED 463
AED 892 total
includes taxes & fees
1 Jul - 2 Jul
Spacious 3BR Family Home Near Everything

Peaceful private 2-bedroom house in Bayport. Amazing location!

Peaceful private 2-bedroom house in Bayport. Amazing location!
Bayport
9.4 out of 10, Exceptional, (6 reviews)
"Patrick is a fantastic host. Super accommodating and attentive! Clean and organized home, comfy bed too!"
United States
Emily D.
The price is AED 1,488
AED 1,943 total
includes taxes & fees
28 Jun - 29 Jun
Peaceful private 2-bedroom house in Bayport. Amazing location!

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 AED 1,355
AED 2,489 total
includes taxes & fees
28 Jun - 29 Jun
Modern Vacation home. Close to The Hamptons

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is AED 1,140
AED 1,311 total
includes taxes & fees
7 Jul - 8 Jul
Guesthouse at Norwalk Inn

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, (44 reviews)
"This place was the perfect location for us. Almost exact center between Jones beach and Port Jefferson. Clean and identical to what is shown."
United States
Marcus
The price is AED 364
AED 604 total
includes taxes & fees
1 Jul - 2 Jul
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.

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 AED 984
AED 2,006 total
includes taxes & fees
29 Jun - 30 Jun
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY

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, (29 reviews)
"Lovely time with so many fun games and activities on the property, highly recommend!"
United States
Logan S.
The price is AED 2,755
AED 5,443 total
includes taxes & fees
26 Jul - 27 Jul
Spacious Family Retreat with Heated Pool, Hot Tub, Sauna, basketball & Golf.

Waterfront house next to Bellport golf course

Waterfront house next to Bellport golf course
East Patchogue
10.0 out of 10, Exceptional, (16 reviews)
"Our stay was wonderful! Everything was clean and the host was very flexible. We would definitely come again for the summer time"
United States
Depp S.
The price is AED 3,489
AED 5,753 total
includes taxes & fees
7 Jul - 8 Jul
Waterfront house next to Bellport golf course

Production Studio - 4 Sets / 2 Offices / Light Bank / Hex Lighting - 4k SF

Production Studio - 4 Sets / 2 Offices / Light Bank / Hex Lighting - 4k SF
West Babylon
The price is AED 3,122
AED 4,528 total
includes taxes & fees
9 Jul - 10 Jul
Production Studio - 4 Sets / 2 Offices / Light Bank / Hex Lighting - 4k SF

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Tranquil Stay

Tranquil Stay
Shirley
8.0 out of 10, Very Good, (10 reviews)
"Great stay! "
United States
Emily S.
The price is AED 1,570
AED 2,675 total
includes taxes & fees
6 Jul - 7 Jul
Tranquil Stay

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)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is AED 1,377
AED 3,231 total
includes taxes & fees
8 Jul - 9 Jul
3 Story Beach Waterview, 3 KING bed, golf putting green!

Bright airy Fair Harbor home with ocean views steps from the soft sandy beach

Bright airy Fair Harbor home with ocean views steps from the soft sandy beach
Fire Island
9.6 out of 10, Exceptional, (4 reviews)
"Perfect Fire Island getaway. Great location and beautiful beach home. Would recommend and love to come back!"
United States
Jessica W.
The price is AED 3,122
AED 4,792 total
includes taxes & fees
29 Jun - 30 Jun
Bright airy Fair Harbor home with ocean views steps from the soft sandy beach

Stareway to Heaven in Fairfield

Stareway to Heaven in Fairfield
2.0 star property
Fairfield Beach
The price is AED 3,548
AED 5,043 total
includes taxes & fees
12 Jul - 13 Jul
Stareway to Heaven in Fairfield

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (12 reviews)
"This house was so lovely, clean, cozy, and well-appointed - everything we could have asked for for a girls' weekend! And so close to the town of Westport with its excellent restaurants and shops. The best!"
United States
Rebecca H.
The price is AED 1,642
AED 3,038 total
includes taxes & fees
12 Jul - 13 Jul
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.8 out of 10, Exceptional, (7 reviews)
"The whole experience was great"
United States
David
The price is AED 390
AED 798 total
includes taxes & fees
29 Jun - 30 Jun
Your Perfect Getaway Between Farmingdale & Amityville
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

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.