Vacation rentals in Shelter Island Heights

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Top-rated vacation rentals in Shelter Island Heights

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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.

Dec 5 – 12

€ 1,036 per night

Guest favorite

Home in Greenport

4.9 out of 5 average rating, 29 reviews

Lovely 1st floor of farmhouse, wineries/downtown

Lovely Victorian home with private entrance, porch, & brick patio. Floor to ceiling windows in light filled large bedroom with en suite bathroom. Cozy den has a beautiful bay window and a queen-size pull-out sofa bed for additional guests. Sunny sitting room just off of the kitchen for reading or games. Full kitchen, washer dryer, high speed internet, and new flat screen TV can be found in the unit. Fantastic restaurants, wineries, beaches are nearby. Enjoy all the North Fork as to offer!

Oct 15 – 22

€ 287 per night

Guest favorite

Apartment in Greenport

4.95 out of 5 average rating, 122 reviews

Upscale Newly Constructed Apartment

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars. It is a week minimum during the peak season ( memorial day weekend until labor day weekend)

Feb 22 – Mar 1

€ 426 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!

Jun 1 – 8

€ 305 per night

Superhost

Home in Greenport

4.94 out of 5 average rating, 136 reviews

Blue Bay Dream - Apt #2

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).

Sep 22 – 29

€ 241 per night

Guest favorite

Guest suite in Sag Harbor

4.95 out of 5 average rating, 188 reviews

Cedar Haven In Sag Harbor

This is a large one room studio apartment with private entrance and ensuite bathroom. The unit is private and closed off from the host’s house. The large main room has a queen bed, and a spacious seating area that includes chairs as well as a comfy leather couch. PLEASE NOTE: One night stays are welcomed but there is a higher rate: IN season, (June 1 - Oct 31) the ONE NIGHT RATE is $375 OFF season, (mid Oct - end of May) the ONE NIGHT RATE is $300

Dec 10 – 17

€ 189 per night

Guest favorite

Home in Shelter Island

4.92 out of 5 average rating, 73 reviews

Family Friendly Island Home

Our easy going and comfortable house has a huge yard with lots of sunshine. Within biking access to beaches, farm stands and a nature preserve, enjoy the country and beach all in one vacation. This is not an anonymous rental its a real home so it's perfect for families with children, there are toys, games, books and art supplies available. There is no AC in the house, though this is usually not a problem on any but the absolute hottest days of summer.

Oct 7 – 14

€ 683 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

€ 555 per night

Guest favorite

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 24 – 31

€ 410 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!!!

Sep 30 – Oct 7

€ 745 per night

Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 584 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!

Oct 5 – 12

€ 169 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

Dec 6 – 13

€ 702 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Shelter Island Heights vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Shelter Island Heights's top sights

American Beech52 locals recommend

Claudio's Waterfront44 locals recommend

Lucharitos51 locals recommend

Claudio's39 locals recommend

SALT Waterfront Bar & Grill34 locals recommend

Crazy Beans21 locals recommend

Other great vacation rentals in Shelter Island Heights

Guest favorite

Guesthouse in Shelter Island

4.95 out of 5 average rating, 22 reviews

Lovely Island Cottage

Dec 15 – 22

€ 415 per night

Guest favorite

Guest suite in Greenport

5.0 out of 5 average rating, 45 reviews

Private Suite in Greenport Historical District

May 30 – Jun 6

€ 285 per night

Guest favorite

Guesthouse in Shelter Island

5.0 out of 5 average rating, 25 reviews

Sleek and Chic cottage/Pool House

Oct 20 – 27

€ 196 per night

Guest favorite

Home in Greenport

4.98 out of 5 average rating, 85 reviews

Designer's Dream - Charming Boathouse

Oct 12 – 19

€ 433 per night

Guest favorite

Apartment in Greenport

4.95 out of 5 average rating, 19 reviews

Farmhouse vibe in heart of Greenport

Feb 1 – 8

€ 473 per night

Guest favorite

Home in Greenport

5.0 out of 5 average rating, 29 reviews

Historic Stunner in Heart of Village

Feb 15 – 22

€ 548 per night

Guest favorite

Cottage in Shelter Island

4.96 out of 5 average rating, 90 reviews

3 Bedroom Cottage Gem

Jul 7 – 14

€ 712 per night

Guest favorite

Cottage in Shelter Island

4.88 out of 5 average rating, 16 reviews

Waterfront Getaway on Shelter Island

Nov 16 – 23

€ 704 per night

Show all

Quick stats about vacation rentals in Shelter Island Heights

Total rentals
290 properties
Rentals with a pool
100 properties have a pool
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
220 properties are a good fit for families
Total number of reviews
8.3K reviews
Nightly prices starting at
€ 94 before taxes and fees

Frequently Asked Questions

Are there Shelter Island Heights vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 100 vacation homes with pools in Shelter Island Heights, available on Airbnb. Make a splash and soak up the sun in style!
Do boutique hotel rentals in Shelter Island Heights have air conditioning?
Absolutely! We offer over 10 boutique hotel rentals with air conditioning in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Shelter Island Heights?
Shelter Island Heights has more than 220 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Shelter Island Heights?
Yes! Work meets play with ease at over 150 vacation rentals in Shelter Island Heights featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Shelter Island Heights?
Experience the best of Shelter Island Heights with our apartment rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do bed and breakfast rentals in Shelter Island Heights have free parking?
Absolutely! We offer over 10 bed and breakfast rentals with free parking in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Shelter Island Heights?
Enhance your stay in our House Rentals with the most popular amenities: over 190 homes with air conditioning, over 190 homes with free parking, over 190 homes with wifi, over 190 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Shelter Island Heights have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Shelter Island Heights have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Shelter Island Heights?
Four-legged friends are welcome in Shelter Island Heights. Choose from more than 110 vacation rentals for guests traveling with pets.

Vacation rentals in Shelter Island Heights

Top-rated vacation rentals in Shelter Island Heights

Vacation rentals for every style

Houses

Apartments

Hotels

Popular amenities for Shelter Island Heights vacation rentals

Stay near Shelter Island Heights's top sights

Other great vacation rentals in Shelter Island Heights

Guesthouse in Shelter Island

Guest suite in Greenport

Guesthouse in Shelter Island

Home in Greenport

Apartment in Greenport

Home in Greenport

Cottage in Shelter Island

Cottage in Shelter Island

Quick stats about vacation rentals in Shelter Island Heights

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 Shelter Island Heights vacation rentals on Airbnb with pools?

Do boutique hotel rentals in Shelter Island Heights have air conditioning?

Are there family-friendly vacation rentals in Shelter Island Heights?

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

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

Do bed and breakfast rentals in Shelter Island Heights have free parking?

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

Do apartment rentals in Shelter Island Heights have a kitchen?

Do cottage rentals in Shelter Island Heights have wifi?

Are there pet-friendly vacation rentals in Shelter Island Heights?

Destinations to explore