Smithtown Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Smithtown vacation rentals

Luxury Room, 1 King Bed, Non Smoking, Air conditioning | Living area | Fireplace

Spacious 3BR Family Home Near Everything

Spacious 3BR Family Home Near Everything
3.5 star property
Central Islip
The price is ￥22,222
￥41,103 total
includes taxes & fees
May 20 - May 21
Spacious 3BR Family Home Near Everything
Exterior

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 ￥22,868
￥97,323 total
includes taxes & fees
May 24 - May 25
Sundown Escape-South Shore Long Island
Apartment (4 Bedrooms) | Interior

Shop, Hike, Golf & Swim: Inviting Deer Park Escape

Shop, Hike, Golf & Swim: Inviting Deer Park Escape
3.0 star property
Deer Park
The price is ￥23,335
￥87,117 total
includes taxes & fees
Jun 4 - Jun 5
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
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, (88 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is ￥27,997
￥41,885 total
includes taxes & fees
May 26 - May 27
DUNE Fairfield Beach
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 ￥42,566
￥86,741 total
includes taxes & fees
May 20 - May 21
Homelike, peaceful and centrally- home located in the hamlet of Rocky Point NY
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
8.8 out of 10, Excellent, (11 reviews)
"Had a great stay "
United States
Desiree
The price is ￥14,295
￥24,822 total
includes taxes & fees
May 20 - May 21
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Exterior detail

East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!

East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!
East Meadow
8.8 out of 10, Excellent, (15 reviews)
"The apartment was very clean and well maintaimed. This was the perfect property to stay at over the holidays as I grew up in the area and had many moments of nostalgia going to old restaurants and shops I frequented as a kid. "
United States
Alexander A.
The price is ￥15,089
￥25,708 total
includes taxes & fees
May 20 - May 21
East Meadow Gem: Cozy 1BR Basement Apt with All the Comforts You Need!
1 bedroom, WiFi

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is ￥30,954
￥60,938 total
includes taxes & fees
May 27 - May 28
Luxe Provincial Style Studio w/ Patio & Parking
1 bedroom, free WiFi, bed sheets

South Shore Studio in Mastic

South Shore Studio in Mastic
Mastic
10.0 out of 10, Exceptional, (4 reviews)
"Really nice and great price! Would stay again. "
United States
Philip P.
The price is ￥21,442
￥36,294 total
includes taxes & fees
May 25 - May 26
South Shore Studio in Mastic
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 ￥21,430
￥37,033 total
includes taxes & fees
May 27 - May 28
Lovely RV with AC in charming Bethpage a mile from the train to NYC
1 bedroom, iron/ironing board, free WiFi, bed sheets

Your Perfect Getaway Between Farmingdale & Amityville

Your Perfect Getaway Between Farmingdale & Amityville
Amityville
9.6 out of 10, Exceptional, (4 reviews)
"It was relaxing very comfortable "
United States
Julian R.
The price is ￥16,868
￥34,514 total
includes taxes & fees
May 21 - May 22
Your Perfect Getaway Between Farmingdale & Amityville
Terrace/patio

The Royal Suite - Ronkonkoma

The Royal Suite - Ronkonkoma
Ronkonkoma
10.0 out of 10, Exceptional, (4 reviews)
"Accommodations were immaculate, very "cozy'. Would stay here again when in the area."
United States
Maureen F.
The price is ￥21,156
￥58,470 total
includes taxes & fees
May 27 - May 28
The Royal Suite - Ronkonkoma
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 ￥29,384
￥58,613 total
includes taxes & fees
May 20 - May 21
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
1 bedroom, desk, WiFi, bed sheets

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is ￥22,554
￥42,297 total
includes taxes & fees
May 20 - May 21
Spacious Studio with Pool Table
Outdoor dining

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Huntington
9.8 out of 10, Exceptional, (7 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is ￥23,030
￥36,113 total
includes taxes & fees
May 27 - May 28
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
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, (40 reviews)
"I found everything to be clean and fresh. Owners were nice. I would stay there again. "
United States
Mark
The price is ￥16,868
￥27,440 total
includes taxes & fees
May 26 - May 27
Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons.
Smart TV

JC Entire Apartment remodeled, close to Airport and Ferry

JC Entire Apartment remodeled, close to Airport and Ferry
Coram
10.0 out of 10, Exceptional, (3 reviews)
"Would definitely stay again "
United States
Katherine R.
The price is ￥13,501
￥32,303 total
includes taxes & fees
Jun 13 - Jun 14
JC Entire Apartment remodeled, close to Airport and Ferry
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)
"Great property, wonderful communication with owner. Would stay here again"
United States
Robert L.
The price is ￥42,725
￥116,864 total
includes taxes & fees
May 26 - May 27
3 Story Beach Waterview, 3 KING bed, golf putting green!
TV

Spacious one Bedroom Apt with private entrance

Spacious one Bedroom Apt with private entrance
Centereach
7.8 out of 10, Good, (10 reviews)
"The place was great. It was clean and spacious, and located on a quiet street. It was also accessible to all the major roads. The host was very accommodating. Very pleased with it all and would highly recommend! "
United Kingdom
Selective Travel M.
The price is ￥17,868
￥54,528 total
includes taxes & fees
May 24 - May 25
Spacious one Bedroom Apt with private entrance
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, (78 reviews)
"Location was perfect!"
United States
Linda J P.
The price is ￥48,443
￥96,538 total
includes taxes & fees
May 21 - May 22
Captain's Cottage - Cold Spring Harbor Water Views
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

Hyatt Regency Long Island

Hyatt Regency Long Island

10/10 Excellent
"Very good location Nice and clean Very kind works. "
Cleison 1-night trip
Posted 1 hour ago
Hyatt Regency Long Island

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?

Cozy Studio near major highways. 45mins from NYC & 60 mins from Hamptons. : This vacation home rental outside of Smithtown has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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.