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.

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Guest favorite

Home in Shelter Island

4.97 out of 5 average rating, 193 reviews

Huge 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.

Oct 21 – 28

$866 per night

Guest favorite

Guest suite in Sag Harbor

4.88 out of 5 average rating, 310 reviews

Artists 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.

Dec 2 – 9

$213 per night

Guest favorite

Apartment in Sag Harbor

4.98 out of 5 average rating, 131 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Oct 3 – 10

$300 per night

Guest favorite

Guest suite in Greenport

4.92 out of 5 average rating, 276 reviews

The Greenport Suite—private entry + near the beach

Welcome to The Greenport Suite! With its separate entrance, secluded outdoor patio space and ideal location, this newly-redesigned private suite in our contemporary Village home is perfect for enjoying a North Fork getaway. We are located just a few short blocks from bay beaches, the harbor, and public transport, while the area's celebrated wineries are a short drive or bike ride away. Come see why Forbes named Greenport one of the 11 prettiest villages in the United States!

Feb 22 – Mar 1

$210 per night

Guest favorite

Home in Greenport

4.92 out of 5 average rating, 422 reviews

Blue Bay Dream - Apt #1

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Dec 5 – 12

$120 per night

Guest favorite

Home in Sag Harbor

4.95 out of 5 average rating, 129 reviews

Luxury Private King Suite + 2 Floor Living Space

Your modern, spacious, sparkling clean guest home has 2 private floors and a private entrance. The bedroom provides luxury and calm as light from the green trees filters in. Watch movies & chill in your living room complete with kitchenette, wine cooler, powder room and adjoining dining space. You’re in a peaceful neighborhood facing a land forest preserve, 5 minutes from bay beaches and the plethora of farm fresh, organic Sag Harbor eateries.

Oct 28 – Nov 4

$369 per night

Guest favorite

Apartment in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

Oct 23 – 30

$650 per night

Guest favorite

Home in Greenport

4.97 out of 5 average rating, 220 reviews

The Greenport Bungalow

Sweet Modern Bungalow Walking Distance to Town Located in the historic town of Greenport Village - 8 min walk to the beach, center of town, Shelter Island Ferry and LIRR... A newly built sun filled 3 bedroom house with all the amenities you would need when renting a home. Enjoy the large and fenced in back yard after a fun day in this historic Long Island fishing village. Great restaurants, and even better locally produced wine and beer!

Aug 20 – 27

$497 per night

Superhost

Home in Shelter Island

4.89 out of 5 average rating, 106 reviews

Hay Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Monday-Thursday stays February through June no cleaning fees!!!

Oct 3 – 10

$656 per night

Guest favorite

Home in Sag Harbor

4.97 out of 5 average rating, 258 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

Sep 10 – 17

$593 per night

Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 585 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

Aug 26 – Sep 2

$174 per night

Guest favorite

Apartment in Shelter Island Heights

4.91 out of 5 average rating, 227 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

Apr 21 – 28

$625 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Shelter Island vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Shelter Island's top sights

SALT Waterfront Bar & Grill34 locals recommend

Mashomack Preserve70 locals recommend

Marie Eiffel Market41 locals recommend

South Ferry Inc.6 locals recommend

The Islander10 locals recommend

Vine Street Café61 locals recommend

Other great vacation rentals in Shelter Island

Guest favorite

Guesthouse in Shelter Island

5.0 out of 5 average rating, 50 reviews

Bayfront 1BR/2BR detached guesthouse with pool

Aug 24 – 31

$350 per night

Guest favorite

Guest suite in Shelter Island

4.89 out of 5 average rating, 28 reviews

Private two-bedroom stay on Shelter Island

May 8 – 15

$300 per night

Guest favorite

Guesthouse in Shelter Island

4.95 out of 5 average rating, 22 reviews

Lovely Island Cottage

Dec 17 – 24

$375 per night

Guest favorite

Home in Shelter Island

5.0 out of 5 average rating, 50 reviews

CASA GYPSEA - a chic and peaceful 3 bedroom house

Dec 20 – 27

$537 per night

Guest favorite

Home in Shelter Island

4.92 out of 5 average rating, 73 reviews

Family Friendly Island Home

Oct 7 – 14

$600 per night

Guest favorite

Cottage in Shelter Island

4.96 out of 5 average rating, 90 reviews

3 Bedroom Cottage Gem

Jul 10 – 17

$621 per night

Superhost

Home in Shelter Island

4.88 out of 5 average rating, 69 reviews

Charming 4BR Cottage on Shelter Island

Nov 7 – 14

$270 per night

Guest favorite

Home in Shelter Island

5.0 out of 5 average rating, 10 reviews

Spacious house with pool.

Sep 14 – 21

$746 per night

Show all

Other great vacation rentals in Shelter Island

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 10 reviews

The Sandy Shack - Coastal Escape

Oct 20 – 27

$570 per night

Guest favorite

Cottage in Sag Harbor

5.0 out of 5 average rating, 29 reviews

Luxury Gem At The Heart of Sag Harbor Village

Jun 23 – 30

$745 per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 35 reviews

Beachfront Greenport Villa

Mar 15 – 22

$517 per night

Guest favorite

Apartment in Clinton

4.98 out of 5 average rating, 49 reviews

Cozy Shoreline Getaway

Jul 13 – 20

$103 per night

Guest favorite

Home in Sag Harbor

5.0 out of 5 average rating, 92 reviews

Secluded Modern Beach Style House

Sep 1 – 8

$745 per night

Guest favorite

Guest suite in Old Saybrook

5.0 out of 5 average rating, 37 reviews

Cozy Loft Getaway

May 29 – Jun 5

$133 per night

Guest favorite

Cottage in Shelter Island

4.94 out of 5 average rating, 32 reviews

Cozy Shelter Island 2 Bedroom 1 Bath Cottage

Jul 25 – Aug 1

$518 per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 29 reviews

Historic Stunner in Heart of Village

Sep 29 – Oct 6

$490 per night

Show all

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
2.7K reviews
Nightly prices starting at
$120 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.
Are there Shelter Island vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 50 vacation homes 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 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 cottage rentals in Shelter Island have air conditioning?
Absolutely! We offer over 10 cottage 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 cottage rentals in Shelter Island?
Experience the best of Shelter Island with our cottage rentals, starting at about $280 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 cottage rentals in Shelter Island?
Shelter Island has more than 10 family-friendly cottage 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.
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 Cottage Rentals in Shelter Island?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Shelter Island vacation rentals

Top-rated vacation rentals in Shelter Island

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Shelter Island vacation rentals

Stay near Shelter Island's top sights

Other great vacation rentals in Shelter Island

Guesthouse in Shelter Island

Guest suite in Shelter Island

Guesthouse in Shelter Island

Home in Shelter Island

Home in Shelter Island

Cottage in Shelter Island

Home in Shelter Island

Home in Shelter Island

Other great vacation rentals in Shelter Island

Home in Greenport

Cottage in Sag Harbor

Home in Greenport

Apartment in Clinton

Home in Sag Harbor

Guest suite in Old Saybrook

Cottage in Shelter Island

Home in Greenport

Quick stats about vacation rentals in Shelter Island

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Shelter Island?

Are there vacation rentals with a dedicated workspace in Shelter Island?

Are there Shelter Island vacation rentals on Airbnb with pools?

Do house rentals in Shelter Island have a gym?

Do cottage rentals in Shelter Island have air conditioning?

How much does it cost to stay in cottage rentals in Shelter Island?

Are there family-friendly cottage rentals in Shelter Island?

Do house rentals in Shelter Island have a bbq area?

Do house rentals in Shelter Island have wifi?

What are the most popular amenities for Cottage Rentals in Shelter Island?

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