Vacation rentals with a patio in Shelter Island

Find and book unique accommodations with an outdoor patio on Airbnb

Top-rated accommodations with an outdoor patio in Shelter Island

Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.

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Guest favourite

Apartment in Mastic

5.0 out of 5 average rating, 17 reviews

The Cozy Cellar | Private Art Deco Apartment

Centrally located 1.5 hours from NYC! We'd love to host you in our Cozy Cellar. Our Art Deco influenced basement apartment is 5 minutes from local groceries, 20 minutes to The Hamptons, 10 minutes from to Center Moriches, 8 minutes to Waterdrinker Farm and 30 minutes to Jamesport and the North Fork. Weekend getaways or Long term stays! We are just 14 minutes from Brookhaven Lab for those looking for a Corporate stay. Furry friends welcome for an additional fee (small fenced in private yard).

Mar. 7 – 14

$106 CAD per night

Guest favourite

Cottage in Westbrook

4.85 out of 5 average rating, 96 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Oct. 13 – 20

$213 CAD per night

Guest favourite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Escape to your own private oasis at this charming beach house in Greenport. This beachfront home offers views of the ocean in every room. Inside, the living space gives plenty of natural light and sitting areas. The kitchen has everything you need to cook for family & friends. There are 4 beds to choose from, which can sleep 6 total. Outside, enjoy your own private beach as well as kayaks to use at your leisure. Located next to Greenport's best restaurants and wineries, book your stay today!

Sep. 13 – 20

$969 CAD per night

Guest favourite

Home in Old Saybrook

4.96 out of 5 average rating, 49 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Relax and enjoy the beach life in this newly renovated charmer just steps from The Saybrook Manor Assoc private beach which is only available to Saybrook Manor Assoc members. Enjoy cooking your favorite family meals in our fully stocked kitchen or venture out to some of the best restaurants on The CT Shore with a short 5-15 min drive. Free wifi for work or entertainment , private outdoor patio dining and serenity await you. You will feel at home in our little slice of heaven on The Shore.

Nov. 9 – 16

$275 CAD per night

Guest favourite

Home in Southold

5.0 out of 5 average rating, 31 reviews

Salt & Sea House - Near wineries, farms, & beaches

Close to beaches, wineries, farms, and restaurants--the Salt and Sea House is a relaxing North Fork getaway for vacations and working from home. Uncork a bottle of wine, start up the barbecue, and settle into the beautiful scenery filled with trees and sounds of the sea. Highlights: * 3 min drive to Goose Creek Beach * 4 min drive to Croteaux Vineyards * 7 min drive to Country View farm * Master bath with tub and rain shower * Large fenced in yard * Pack & Play and toys

Sep. 18 – 25

$694 CAD per night

Guest favourite

Cottage in Shelter Island

4.88 out of 5 average rating, 16 reviews

Waterfront Getaway on Shelter Island

This bright, spacious, private 3 bedroom, 2 bath contemporary home located at the end of the secluded Westmoreland peninsula on Shelter Island is the ideal retreat for summer. Hosting waterfront views from every room leading to a large open deck for gatherings of all kinds. This remote cottage is only 5 minutes from 2 of the best beaches on Shelter Island, Shell and Crescent Beach. Bring your water sports and enjoy Westneck creek and it’s beautiful scenic views!

Dec. 3 – 10

$1,036 CAD per night

Guest favourite

Cottage in Shelter Island

4.94 out of 5 average rating, 32 reviews

Cozy Shelter Island 2 Bedroom 1 Bath Cottage

This cozy cottage is perfect place to relax and unwind. Located in the center of the island about a mile from the beach and nature preserve. Sleeps up to 9 people - with queen size aero bed provided. Linens, dishes, utensils etc. included. Fridge has icemaker and filtered water feature. Outdoor covered dining area with table and 6 chairs. 2 person swing, BBQ & outdoor shower. 2/3 acre property. Relax with the whole family at this peaceful place to stay.

Jun. 10 – 17

$742 CAD per night

Guest favourite

Home in Mattituck

4.92 out of 5 average rating, 92 reviews

Modern Farmhouse Steps to Beach & Love Lane

Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.

Feb. 14 – 21

$689 CAD per night

Guest favourite

Cottage in East Hampton

5.0 out of 5 average rating, 20 reviews

Chic cottage on lush, secluded acre by the beach.

Charming cottage with spacious lawn surrounded by lush vegetation and protected land. 5-minute walk to a secluded and serene Northwest Harbor beach. An approximately 10-minute drive from both East Hampton and Sag Harbor restaurants and stores. Chic and modern rooms with brand-new, high-end bathrooms. Perfect rental for those who want a mix of quiet time and quick access to everything else. Relax and unwind at this unique and tranquil getaway.

Dec. 2 – 9

$540 CAD per night

Guest favourite

Home in Cutchogue

5.0 out of 5 average rating, 24 reviews

North Fork paradise between beaches and vineyards

Kick back and relax in this calm, stylish retreat. Nestled between vineyards and farmlands, this newly renovated mid-century ranch with a beautiful 14x50' heated salt water pool is a short hop to beautiful beaches, wineries, restaurants, and farm stands. Enjoy nature in a secluded park-like setting and explore everything the NoFo has to offer all year around. Please note that there are no parties, gatherings or unannounced guests allowed.

Nov. 7 – 14

$923 CAD per night

Guest favourite

Guesthouse in Shelter Island

5.0 out of 5 average rating, 50 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Perfect relaxing getaway for a couple or family. Bayfront 1BR/2BR fully detached guest house with gorgeous morning views. Property has saltwater pool + hot tub (open May -October) and bay access via private dock. Central to both north & south forks (wineries + Hamptons or Montauk just short drive away). Down the road from famous Shelter Island Sunset Beach + golf course. Come explore the beauty of the Hamptons without the stress!

Aug. 3 – 10

$603 CAD per night

Guest favourite

Tiny homes in East Lyme

5.0 out of 5 average rating, 102 reviews

Luxury Tiny Home Near Rocky Neck

Home away from home at our chic hideaway! Create a culinary masterpiece in the fully-appointed kitchen. Pamper yourself with heated floors in the bathroom, outdoor fire pit and heater. An elevated platform perfect for camping or yoga. Nestled just minutes from the picturesque Rocky Neck and McCooks beach, this is the ultimate small family romantic retreat or solo experience!

Sep. 26 – Oct. 3

$534 CAD per night