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Check prices for these dates

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

Our top choices for Smithtown holiday 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 3.689.016 ₫
6.823.549 ₫ total
includes taxes & fees
20 May - 21 May
Spacious 3BR Family Home Near Everything
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 4.645.164 ₫
6.949.410 ₫ total
includes taxes & fees
26 May - 27 May
DUNE Fairfield Beach
House (3 Bedrooms) | Interior

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 8.643.456 ₫
16.228.089 ₫ total
includes taxes & fees
24 May - 25 May
Charming Rocky Point Home ~ 1 Mi to Beach!
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 3.873.744 ₫
16.245.285 ₫ total
includes taxes & fees
24 May - 25 May
Sundown Escape-South Shore Long Island
Standard Room, 1 King Bed, Main Building | Property entrance

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 9.460.368 ₫
10.879.424 ₫ total
includes taxes & fees
19 May - 20 May
Guesthouse at Norwalk Inn
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 3.873.744 ₫
14.461.978 ₫ total
includes taxes & fees
29 May - 30 May
Shop, Hike, Golf & Swim: Inviting Deer Park Escape
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

The Circle Hotel Fairfield

The Circle Hotel Fairfield

8/10 Good
"Clean and convenient location. Wish it had a place for our luggage other than the floor."
todd 1-night trip
Posted 5 hours ago
The Circle Hotel Fairfield

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Frequently asked questions

Are there holiday rentals in Smithtown?

Yes, there are holiday rentals in Smithtown close to Blydenburgh County Park, or you can select a more secluded option if you're looking for a relaxing stay. Smithtown is known for its lake views.

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 holiday rentals like in Smithtown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Smithtown. Holiday rentals feature amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for small groups.