Shelter Island vacation rentals
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Top-rated vacation rentals in Shelter Island
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Cottage in Riverhead
4.98 out of 5 average rating, 126 reviewsSavor Blazing Ocean Sunsets at a Soothing Beachfront Haven
Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.
Mar 26 – Apr 2
Home in Shelter Island
4.97 out of 5 average rating, 189 reviewsHuge Island Getaway Pool HotTub Walk To Beach
Relaxation begins on the 6 minute ferry ride to this magical island. Summerfield is a spectacular, grand compound that has it all. Huge main house great for groups, 4700ft w/ privacy for all overlooking serene nature reserve. Star gaze in the bubbling hot tub, grill outside after a swim, play in the rec room with movie theater, pool table or ping pong,or watch TV by the fire! Open plan layout, gourmet kitchen, heated gunite pool, separate guest house. Prime location close to beach + restaurants.
Jan 27 – Feb 3
Guest suite in Sag Harbor
4.88 out of 5 average rating, 308 reviewsArtists Sag Harbor Village Retreat
January special -book second night for $125! This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.
Nov 29 – Dec 6
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Shelter Island vacation rentals
Shelter Island house rentals
Home in Sag Harbor
4.97 out of 5 average rating, 123 reviewsRelax into Coastal Life at a Sun-Drenched Sag Harbor Home
Sep 14 – 21
Home in Sag Harbor
4.95 out of 5 average rating, 129 reviewsLuxury Private King Suite + 2 Floor Living Space
Apr 9 – 16
Home in East Hampton
4.96 out of 5 average rating, 187 reviewsRitz-East Hampton Cottage- 5 stars
Sep 13 – 20
Home in East Hampton
4.93 out of 5 average rating, 138 reviews1800 Historical East Hampton Home, 1 Mile to Town!
Feb 24 – Mar 3
Home in East Marion
4.98 out of 5 average rating, 107 reviewsStylish Farmhouse in North Fork
Jan 30 – Feb 6
Home in Shelter Island
5.0 out of 5 average rating, 50 reviewsCASA GYPSEA - a chic and peaceful 3 bedroom house
May 12 – 19
Home in Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
Jan 24 – 31
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
Oct 25 – Nov 1
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
Dec 5 – 12
Home in Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
Nov 4 – 11
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
Mar 9 – 16
Home in Shelter Island
4.88 out of 5 average rating, 68 reviewsCharming 4BR Cottage on Shelter Island
May 27 – Jun 3
Other great vacation rentals in Shelter Island
Apartment in Greenport
4.97 out of 5 average rating, 194 reviewsGreenport Village View - Walkable 2BR Stay
Feb 7 – 14
Guesthouse in Sag Harbor
4.84 out of 5 average rating, 115 reviewsSag Harbor Cottage in historic district
Oct 26 – Nov 2
Condo in Greenport
4.91 out of 5 average rating, 107 reviewsBeachside Waterview 2Br Condo w/ Pool in Greenport
May 12 – 19
Apartment in Sag Harbor
4.99 out of 5 average rating, 128 reviewsUpdated apartment in historic village home
May 10 – 17
Guest suite in Shelter Island
4.89 out of 5 average rating, 28 reviewsPrivate two-bedroom stay on Shelter Island
Jun 5 – 12
Guesthouse in Shelter Island
5.0 out of 5 average rating, 50 reviewsBayfront 1BR/2BR detached guesthouse with pool
Jul 22 – 29
Guesthouse in Shelter Island
4.95 out of 5 average rating, 22 reviewsLovely Island Cottage
Nov 26 – Dec 3
Cottage in Shelter Island
4.96 out of 5 average rating, 90 reviews3 Bedroom Cottage Gem
Jun 18 – 25
Cottage in Shelter Island
4.88 out of 5 average rating, 16 reviewsWaterfront Getaway on Shelter Island
Oct 18 – 25
Cottage in Sag Harbor
5.0 out of 5 average rating, 27 reviewsLuxury Gem At The Heart of Sag Harbor Village
May 10 – 17
Home in Greenport
5.0 out of 5 average rating, 32 reviewsBeachfront Greenport Villa
Nov 7 – 14
Cottage in Sag Harbor
4.94 out of 5 average rating, 51 reviewsSteps to the Beach - Designer Cove House Cottage
May 6 – 13
Quick stats about vacation rentals in Shelter Island
Total rentals | 140 properties |
---|---|
Rentals with a pool | 50 properties have a pool |
Pet-friendly rentals | 50 properties allow pets |
Family-friendly rentals | 100 properties are a good fit for families |
Total number of reviews | 3K reviews |
Nightly prices starting at | R2,275 ZAR before taxes and fees |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Shelter Island?
Four-legged friends are welcome in Shelter Island. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Shelter Island?
Yes! Work meets play with ease at over 60 vacation rentals in Shelter Island featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Shelter Island have a gym?
Absolutely! We offer over 10 house rentals with a gym in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shelter Island have air conditioning?
Absolutely! We offer over 90 house rentals with air conditioning in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Shelter Island?
Experience the best of Shelter Island with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Shelter Island?
Shelter Island has more than 90 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Shelter Island have a bbq area?
Absolutely! We offer over 70 house rentals with a bbq area in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
Are there Shelter Island house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 house rentals with pools in Shelter Island, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Shelter Island have wifi?
Absolutely! We offer over 100 house rentals with wifi in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Shelter Island?
Enhance your stay in our House Rentals with the most popular amenities: over 90 homes with air conditioning, over 10 homes with a gym, over 70 homes with a bbq area, over 100 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Family-friendly rentals Shelter Island
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