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Best Vacation rentals and Airbnb offers in Shelter Island, NY
9.2 18 reviews
Shelter Island, NY
06/30 – 07/07
$650/nighttotal: $4550 (7 )
North Fork Cottages & Rv Resort
1 2
resort , Greenport
North Fork Cottages & RV Resort in Greenport offers convenient access to local attractions, located under 2 miles from Kontokosta Winery and 67 Steps Beach, and within easy reach of Eastern Long Island Hospital and Stony Brook Eastern Long Island Hospital. This resort provides amenities such as a seasonal outdoor pool, barbecue grills, a picnic area, free WiFi, and private yards with patios, with accommodations featuring refrigerators, microwaves, and coffee makers.
9.0 1 review
Shelter Island, NY
06/30 – 07/07
$2215/nighttotal: $15505 (7 )
Cozy Greenport Cottage
1 2
house , Greenport
This Greenport vacation rental is located 26 miles from Splish Splash and 47 miles from Long Island MacArthur Airport. This 1700 square foot house features 3 bedrooms, 2 bathrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, an outdoor pool, a sauna, and a patio with an outdoor fireplace, accommodating up to 19 guests.
9.8 11 reviews
Shelter Island, NY
06/30 – 07/07
$740/nighttotal: $5180 (7 )
Beechwood Cottage 1bd
1 2
apartment , Greenport
This modern cottage is located in a quiet district of Greenport, offering easy access to the village center and waterfront attractions. This apartment rental features one bedroom and one bathroom, accommodating up to four guests with a full kitchen, air conditioning, a swimming pool, garden, and grill, perfect for enjoying the Greenport atmosphere.
10 1 review
Shelter Island, NY
06/30 – 07/07
$1711/nighttotal: $11977 (7 )
Bright Beach House With Private Beach Access
4 2
apartment , Shelter Island Heights
This Shelter Island Heights vacation home is near Crescent Beach, a short drive from the Pridwin Hotel and Leon's restaurant. This four-bedroom, two-bathroom house sleeps ten, features a fully equipped kitchen with high-end appliances, multiple outdoor spaces including decks and a screened porch, and provides private beach access for swimming, kayaking, and paddle boarding.
9.3 3 reviews
Shelter Island, NY
06/30 – 07/07
$793/nighttotal: $5551 (7 )
2-bedroom Beechwood Cottage
2 2
cabin , Greenport
This modern cottage is situated on over 23 acres at the easternmost tip of Long Island's North Fork in Greenport, offering a secluded luxury escape. This two-bedroom, one-bathroom cabin accommodates up to six guests and features a full kitchen, air conditioning, internet, and private access to resort amenities including a heated pool and pickleball courts.
9.9 20 reviews
Shelter Island, NY
07/28 – 07/31
$576/nighttotal: $1728 (3 )
2-bedroom Park Model Cottage
1 2
cabin , Greenport
This luxury park model, offering an outdoor escape, is located on over 23 acres at the eastern tip of Long Island's North Fork in Greenport. Accommodating up to 6 guests, this cabin features 2 bedrooms, 1 bathroom, air conditioning, internet, a kitchen, parking, and access to resort amenities including a heated pool and pickleball courts.
9.3 52 reviews
Shelter Island, NY
07/28 – 07/31
$304/nighttotal: $912 (3 )
All Seasons Rental
2 2
apartment , Shelter Island
This Shelter Island country ranch is located near Mashomack Preserve, a five-minute drive from its hiking trails, beaches, and miniature golf. This two-bedroom, one-bathroom house sleeps four and features a full kitchen with dishwasher, in-unit laundry, a relaxing deck, and ample living space.
Shelter Island, NY
06/30 – 07/07
$1438/nighttotal: $10066 (7 )
Modern On 9th
3 2
apartment , Greenport
This dog-friendly apartment in Greenport, New York, offers a unique historical stay, formerly a 1957 candy and soda shop, and is located less than 1 mile from the Shelter Island Ferry, 2 miles from 67 Steps Beach, 6 miles from Sparkling Pointe Vineyards & Winery, and 7.5 miles from Pindar Vineyards. This 3-bedroom, 3-bathroom residence accommodates up to 6 guests with amenities including a modern kitchen with stainless steel appliances, central air conditioning, two fireplaces, and a private backyard, with bikes provided for exploring the surrounding wineries and Orient Beach State Park.
10 19 reviews
Shelter Island, NY
06/30 – 07/07
$4728/nighttotal: $33096 (7 )
Beautiful Sag Harbor Beach House W/pool & Jacuzzi!
4 2
apartment , Sag Harbor
This Hamptons Beach Home is located just a short walk from Havens Beach and a half mile from the charming town center of Sag Harbor, offering easy access to both the beach and local amenities. The property consistently receives excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay. This spacious home features four bedrooms and three bathrooms, comfortably accommodating up to 12 guests. Enjoy a private pool, hot tub, outdoor games, and a hammock, as well as a chef's kitchen, a laundry room, and his-and-hers bikes for exploring the beautiful surrounding area.
9.1 249 reviews
Shelter Island, NY
07/28 – 07/31
$670/nighttotal: $2010 (3 )
The Cliffside Resort Condominiums
1 2
apartment , Greenport
This Greenport apartment is located just a short drive from downtown Greenport and the Hortons Point Lighthouse, offering easy access to the area's attractions. The apartment is highly rated for its cleanliness, location, and overall experience. The two-bedroom apartment spans 550 square feet and provides a comfortable space for your stay. Guests can enjoy amenities like a swimming pool, a private beach, and a terrace, as well as convenient features like a kitchen, air conditioning, and free Wi-Fi.
9.9 49 reviews
Shelter Island, NY
07/28 – 07/31
$897/nighttotal: $2691 (3 )
The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
1 2
apartment , Southold
This three-bedroom, two-bathroom Southold home, a lovingly restored saltbox-style house, is situated near nature preserves, vineyards, and breweries, a short five-minute drive from Greenport Village and Southold. This family-friendly rental boasts a fully equipped kitchen with high-end appliances, a spacious layout accommodating five guests, and extensive outdoor amenities including a firepit, grill, kayaks, and bicycles for exploring the area.
Shelter Island, NY
06/30 – 07/07
$2983/nighttotal: $20881 (7 )
Chic Coastal Farmhouse With Private Pool, Steps From The Water Your...
4 2
apartment , Shelter Island Heights
This Shelter Island Heights vacation home, near Shelter Island's beaches and conveniently located for easy access to the Hamptons and East Hampton Main Beach, offers a luxurious farm stay experience. This 2160-square-foot property boasts three bedrooms and three bathrooms, accommodating up to six guests, and features private pools and in-room kitchens, along with on-site laundry facilities, BBQ grills, and smart TVs in each room.
Best Shelter Island, NY vacation rentals with a balcony
Shelter Island, NY
06/30 – 07/07
$3385/nighttotal: $23695 (7 )
Villa Ebrar - Luxury With Pool
4 2
house , Noyack
This 4-bedroom villa is situated in Sag Harbor, just a short drive from Foster Memorial Beach and Montauk Point Lighthouse, offering easy access to the area's attractions. It has received excellent user ratings, making it a popular choice for travelers. The 3,000 square foot house offers ample space for families and groups. Enjoy a private pool, a fully equipped kitchen, and a terrace, plus amenities like a tennis court, parking, and room service.
9.0 41 reviews
Shelter Island, NY
06/30 – 07/07
$883/nighttotal: $6181 (7 )
Bright And Spacious Summer Home Steps From The Beach
4 2
apartment , Shelter Island Heights
This beach house is located in Hay Beach, a neighborhood on Shelter Island, a short distance from Menhadden Lane Beach and Mashomack Preserve. It has received excellent user ratings, making it a popular choice for travelers. This 4,080 square foot home comfortably accommodates 10 guests in its four bedrooms and three bathrooms. The house features amenities like a private beach, a dock, a grill, and modern technology for entertainment, along with a garden, a terrace, and a jacuzzi.
Shelter Island, NY
07/28 – 07/31
$3100/nighttotal: $9300 (3 )
Relaxing Greenport Escape, Heated Pool, Private Beach Access Steps From The Home
4 2
apartment , Southold
This Southold beach house, located on a private block, is a 5-minute drive from Greenport and Southold, offering convenient access to local shops, restaurants, and vineyards. This 4-bedroom, 2-bathroom vacation rental sleeps up to 9 guests and features a heated private outdoor pool, private beach access, a fire pit, four adult bicycles, and a stand-up paddle board, with central air conditioning and a well-equipped kitchen for your comfort.
10 2 reviews
Shelter Island, NY
06/30 – 07/07
$802/nighttotal: $5614 (7 )
Spacious 5 Bedroom Family Beach Getaway In Charming East Marion/greenport
4 2
apartment , East Marion
This East Marion condo offers a 7-minute walk to Island's End Golf and Country Club and is a 2-minute drive from Kontokosta Winery. This 4-bedroom, 3-bathroom vacation rental accommodates up to 10 guests, featuring a full kitchen with microwave and dishwasher, air conditioning, Wi-Fi, and on-site parking.
Our Favorite Family-Friendly Vacation Rentals in Shelter Island, NY
Plan the perfect family beach trip to Shelter Island, NY with spacious rentals that offer plenty of room to spread out.
This East Marion beachfront home, a short 6-minute drive from Greenport village and 13 minutes from Orient Beach State Park, offers private Gardiner's Bay access with a mooring. The two-house property sleeps eight guests across three bedrooms and three bathrooms, boasting fully equipped kitchens, kayaks, paddleboards, bikes, and family-friendly amenities like children's toys and games.
Shelter Island, NY
07/28 – 07/31
$660/nighttotal: $1980 (3 )
The Chequit
1 2
island , Shelter Island Heights
The Chequit Hotel is situated in the tranquil surroundings of Shelter Island Heights, within easy reach of the Shelter Island Country Club and the historic Sylvester Manor. The hotel offers 35 cozy guestrooms with blackout drapes for privacy, as well as a range of amenities including an on-site restaurant, coffee shop, free Wi-Fi and self-parking.
9.4 12 reviews
Shelter Island, NY
07/28 – 07/31
$1026/nighttotal: $3078 (3 )
Renovated Townhouse Walk To All
4 2
apartment , Greenport
This vacation home is located near the beach in Greenport, within a 10-minute walk of the Greenport Farmers' Market, Railroad Museum of Long Island, and Camera Obscura. It has received very good user ratings. This three-bedroom home comfortably sleeps eight guests. The house offers a fireplace, a patio, a garden, and a kitchen equipped with a refrigerator, oven, microwave, and dishwasher, as well as air conditioning, internet, and parking.
10 5 reviews
Shelter Island, NY
07/28 – 07/31
$1045/nighttotal: $3135 (3 )
Northfork Townhouse Walk To All
4 2
apartment , Greenport
This 3-bedroom house is conveniently located in central Greenport, within a 10-minute walk of the Greenport Farmers' Market, Railroad Museum of Long Island, and Camera Obscura. The home comfortably accommodates 6 guests and offers a fully equipped kitchen, outdoor barbecue grills, a garden, and free WiFi.
Frequently Asked Questions about vacation rentals in Shelter Island, NY
What are some interesting places to visit in or near Shelter Island, NY?
Shelter Island is known for its beautiful beaches, so a visit to Mashomack Preserve is a must. You can also check out the historic Shelter Island Historical Society Museum. If you're looking for something a little more lively, head over to Greenport on the North Fork, which is just a short ferry ride away.
What are the best Airbnb and vacation rentals in Shelter Island, NY?
Which walking or cycling routes are the best in Shelter Island, NY?
The Shelter Island Country Club has a beautiful 3-mile loop that's perfect for a leisurely walk or bike ride. You can also enjoy the scenic views along the Shelter Island Bike Path, which runs for about 5 miles along the island's western shore.
What are the most popular Airbnbs in Shelter Island, NY?
What sports or outdoor activites can visitors enjoy in and around Shelter Island, NY?
Shelter Island is a great place for swimming, kayaking, and fishing. You can also rent a boat and explore the surrounding waters. If you're looking for something more challenging, try hiking at the Mashomack Preserve, which has over 1,000 acres of trails.
What are the best vacation rentals with a pool in Shelter Island, NY?
What other towns or cities can be easily accessed from Shelter Island, NY?
Greenport is a popular destination on the North Fork, and it's easily accessible by ferry from Shelter Island. You can also take the ferry to Sag Harbor, which is known for its charming waterfront and historic buildings. If you're looking for a bigger city, New York City is about a 2-hour drive from Shelter Island.
What are the best rentals for families and kids in Shelter Island, NY?
What amenities are commonly available in vacation rentals in Shelter Island, NY?
Most vacation rentals in Shelter Island offer amenities like air conditioning, WiFi, and laundry facilities. Many also have private decks or patios, fireplaces, and access to swimming pools. Some rentals even come with boats or kayaks.
What are the best rentals or Airbnbs with a jacuzzi in Shelter Island, NY?
What time of year is best to rent a vacation rental Shelter Island, NY?
The best time to visit Shelter Island depends on what you're looking for. Summer is the most popular time to visit, but it can get crowded. If you're looking for a more relaxed experience, spring or fall are great options. The weather is still pleasant, and the crowds are smaller.
Destinations nearby
Best Shelter Island, NY vacation rentals with parking
9.8 115 reviews
Shelter Island, NY
07/28 – 07/31
$717/nighttotal: $2151 (3 )
'The Gate House'on Beach Front Estate With Dockage. Walk To Village .
2 2
cottage , Greenport
This Pipes Cove beach house offers direct beach access, a short walk from Greenport's Railroad Museum and East End Seaport Maritime Museum, and less than a mile from the Camera Obscura and Greenport Carousel. The 850-square-foot home features three bedrooms, one bathroom, sleeps four, and includes a fully equipped kitchen, air conditioning, Wi-Fi, a swimming pool, a terrace, a garden, and on-site parking.
9.0 249 reviews
Shelter Island, NY
07/28 – 07/31
$658/nighttotal: $1974 (3 )
Cliffside Resort Condominiums
1 2
resort , Greenport
Cliffside Resort Condominiums offers beachfront apart-hotel accommodations in Greenport, New York, situated within 3.1 miles of Kontokosta Winery, 67 Steps Beach, and Norman E. Klipp Marine Park. This resort provides apartments with complimentary WiFi, air conditioning, a basic kitchen, two bathrooms, a seating area, and furnished balconies, along with on-site amenities including a swimming pool, garden, and parking, and allows pets.
Shelter Island, NY
06/30 – 07/07
$1448/nighttotal: $10136 (7 )
Haven On Glynn By Rove Travel | 3br Coastal Luxury
3 2
apartment , Shelter Island Heights
This Shelter Island Heights rental is located within 1 mile of Sylvester Manor, Havens House, and Shelter Island Country Club. This apartment offers air conditioning, a balcony, a garden, and a kitchen equipped with a fridge, microwave, and dishwasher, with parking available.
10 3 reviews
Shelter Island, NY
07/28 – 07/31
$704/nighttotal: $2112 (3 )
Surrounded By Nature, Come Stay In This 2 Bedroom Private, Serene Location
2 2
apartment , Southold
This private Southold apartment offers a serene escape adjacent to a 24-acre preserve, with The Hamptons Beaches and Cooper's Beach accessible. This newly finished basement dwelling accommodates two guests with a queen bed, a full kitchen, complimentary bicycles, and kayak/paddleboard access.
Browse Vacation Rentals with a Pool in Shelter Island, NY
Complement your beach days with a dip in the pool at these premier vacation rentals in Shelter Island, NY.
Shelter Island, NY
06/30 – 07/07
$4978/nighttotal: $34846 (7 )
Sun-filled, Custom-designed 5-bedroom Sag Harbor
1 2
apartment , North Haven
This Sag Harbor residence is located in the exclusive North Haven Manor, offering private beach access and proximity to the Peconic River, with downtown Sag Harbor amenities a short drive away. This 3,100 sq. ft. house accommodates 8 guests with 5 bedrooms, 3 bathrooms, a heated Gunite pool and spa, and stunning sunrise and sunset views over Shelter Island Sound and Sag Harbor Cove.
10 4 reviews
Shelter Island, NY
07/28 – 07/31
$3163/nighttotal: $9489 (3 )
Spacious North Fork Home In Greenport, Heated Pool, Perfect For Families
4 2
apartment , Shelter Island Heights
This four-bedroom, 3.5-bathroom house rental in Greenport, on Long Island's North Fork, is a short drive from Shelter Island Heights and offers easy access to beaches like HOA Beach and Southold Town Beach. The 4-bedroom home features a private heated pool and hot tub, multiple indoor/outdoor dining areas, a dedicated workspace, a gas BBQ, and accommodates up to eight guests; StayMarquis management provides 24/7 support.
Shelter Island, NY
06/30 – 07/07
$3344/nighttotal: $23408 (7 )
Chic Coastal Farmhouse, Pool, Steps From Water
4 2
apartment , Shelter Island Heights
This stylish Shelter Island Heights farmhouse, located on Big Ram Island, is a half-mile walk from the Rams Head Inn and Reel Point Beach, offering easy access to Coecles Harbor and other attractions. The three-bedroom, three-bathroom house features a private heated pool, expansive fenced yard, gourmet kitchen, two work-from-home spaces, and can comfortably accommodate six guests, with all the amenities for a relaxing Shelter Island getaway.
Shelter Island, NY
06/30 – 07/07
$2009/nighttotal: $14063 (7 )
The Gathering House | North Fork Retreat
1 2
apartment , East Marion
This East Marion residence offers modern coastal architecture with dramatic double-height ceilings and walls of glass, featuring a luxurious open-concept living space with a floor-to-ceiling fireplace, a chef's kitchen with a massive waterfall island, and seamless indoor-outdoor living. Situated a short distance from beaches, award-winning wineries, farm stands, and waterfront villages like Greenport, this home is ideal for gatherings and relaxation, with the Orient Point Ferry also nearby for convenient day trips. This spacious dwelling accommodates up to 10 guests and boasts a resort-style swimming pool, an outdoor kitchen, and a loft lounge providing a separate relaxation area. The primary suite includes a king bed, an ensuite bathroom with a soaking tub, and direct porch access, complemented by premium stainless steel appliances throughout the chef's kitchen.
Top-Rated Oceanfront Vacation Rentals in Shelter Island, NY
Relax near the shore in these coastal Shelter Island, NY vacation rentals, combining comfortable amenities with beautiful seaside scenery just moments away.
9.7 187 reviews
Shelter Island, NY
07/28 – 07/31
$384/nighttotal: $1152 (3 )
Quiet Neighborhood And Only Steps To Town
1 2
apartment , Greenport
Shelter Island, NY
07/28 – 07/31
$3065/nighttotal: $9195 (3 )
Waterfront Tranquility Near Sag Harbor Village
4 2
apartment , Noyack
Shelter Island, NY
06/30 – 07/07
$1100/nighttotal: $7700 (7 )
Waterfront Jewel Box On A High Bluff.
1 2
apartment , Shelter Island Heights
9.9 75 reviews
Shelter Island, NY
07/28 – 07/31
$661/nighttotal: $1983 (3 )
Beautifully Renovated 2 Bedroom, 1st Floor Apt -Greenport Village, Walk To Town!
1 2
apartment , Greenport
Top-Rated 5-Star Vacation Rentals in Shelter Island, NY
These high-end vacation rentals in Shelter Island, NY offer luxury living and unmatched quality near the shore.
9.7 26 reviews
Shelter Island, NY
07/28 – 07/31
$1079/nighttotal: $3237 (3 )
Beautiful Home On Shelter Island
1 2
apartment , Shelter Island
Best Vacation Rentals with a Steam Room in Shelter Island, NY
Relax with an on-site sauna at these vacation rentals in Shelter Island, NY, perfect for a steam session after a day by the water.
