
Holiday rentals in Shelter Island Heights
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Top-rated holiday rentals in Shelter Island Heights
Guests agree: these stays are highly rated for location, cleanliness and more.

Hamptons Oceanfront Oasis
Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Modern Farmhouse Oasis in GP Village
Newly renovated modern farmhouse with the perfect blend of style & comfort. Bask in the serenity of our fully equipped 600 sq ft deck and outdoor oasis. Charming Greenport Village is a 10 min walk with its vibrant mix of restaurants, bars, & shops. Walk to Claudio’s, Jitney, train, & ferry to Shelter Island. 5 min drive: beaches, winery, golf. Embrace the coastal, farm, and winery allure by unwinding in our thoughtfully designed home, where every detail is tailored for a memorable stay.

The Sandpiper
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).

3 Min Walk to Beach|Close to Town| Fam-Friendly
<b>The Greenport Beach Cottage</b> Rated 5.0 ⭐️by 50+ Reviews | Top 5% of All Airbnbs ✔️ Newly renovated 800 sq ft coastal cottage ✔️ 3 minute walk to beach, 4 minute drive to town ✔️ Sleeps up to 5 guests ✔️ Family- & Dog-Friendly ✔️ Backyard with 2 fire pits, charcoal & gas grill, outdoor shower ✔️ Garage with 4 beach cruiser bikes, Foosball table & small gym area Book your coastal getaway now- summer dates are booking up! IG: @thegreenportbeachcottage

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!

Junior 1-BR in the heart of Greenport Village
Beautiful junior one bedroom in the heart of Greenport Village. Located in the historical district, our basement apartment is walking distance (2-Blocks) to downtown Greenport. Perfect for a couples weekend, girls trip, or for a small family. Our apartment includes one queen bed and a twin day bed with trundle underneath. (Sleeps 4 total) TV with streaming service and WiFi are included. W/D are available upon request.

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.

Hamptons - Shelter Island Farmhouse
Kid friendly! Perfect two family split! Come enjoy our island retreat. Relax with the whole family at this peaceful pad. You will be 2 min on bike from Wades Beach. You can also walk to the best BBQ/seafood in Shelter, Commander Codys. Features a large open kitchen/dining room plus also a spacious living room. 4 bedrooms with new mattresses, huge outdoor patio for family BBQs. No dogs please.

North Fork Waterfront Escape · Sunset Views
Enjoy spectacular views of Hashamomuck Inlet off Shelter Bay from the living room, kitchen, deck, garden, and private dock of this newly renovated 3-bedroom home. With 90 feet of waterfront and a small sandy beach, it's ideal for kayaking, clamming, and swimming — perfect for families with young children. Relax with sunsets, barbecues, and local North Fork wine. The perfect family getaway!

Peaceful Bright Country House
Centrally located bright, and spacious three-bedroom home 10-minute walk to Crescent Beach and town for shopping and cafes. Nice backyard for barbecue Enjoy a peaceful stay at this quiet and colorful country home on beautiful Shelter Island. 1-minute walk to Léon 1909 restaurant and the Tuck Shop for ice cream. 2-minute drive to historic Goat Hill public golf course. NO PETS PLEASE

Laid Back Relaxation
Kick back and relax in this calm, stylish space. Nice newly updated home on a quiet street within walking distance to beaches, restaurants and a golf course. Great location near Shelter Island heights town, Crescent beach and Sunset beach. The location provides both privacy and relaxation at home with just a short walk or ride to popular Shelter Island spots.

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
Popular amenities for Shelter Island Heights holiday rentals
Other great holiday rentals in Shelter Island Heights

Waterfront Treehouse with Pool as seen on HBO

Victorian Pearl

Family Friendly Island Home

Shelter Island Waterfront Getaway

Cosy North Fork Cottage with large backyard

Stylish Studio Suite on Shelter Island

All Seasons Rental

North Fork Paradise
When is the best time to visit Shelter Island Heights?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £262 | £271 | £279 | £280 | £336 | £383 | £443 | £448 | £376 | £321 | £287 | £271 |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Shelter Island Heights?
Shelter Island Heights has more than 350 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Shelter Island Heights?
Experience the best of Shelter Island Heights with our house rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Shelter Island Heights?
Four-legged friends are welcome in Shelter Island Heights. Choose from more than 140 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Shelter Island Heights?
Yes! Work meets play with ease at over 210 vacation rentals in Shelter Island Heights featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Shelter Island Heights condo rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 condo rentals with pools in Shelter Island Heights, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Shelter Island Heights?
Make yourself at home in Shelter Island Heights by choosing from our most frequently booked neighborhoods. We have over 1,630 vacation rentals in Shelter Island, over 990 vacation rentals in Shelter Island Heights, and over 510 vacation rentals in Greenport.
Do house rentals in Shelter Island Heights have air conditioning?
Absolutely! We offer over 280 house rentals with air conditioning in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Shelter Island Heights have a kitchen?
Absolutely! We offer over 30 apartment rentals with a kitchen in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shelter Island Heights have wifi?
Absolutely! We offer over 280 house rentals with wifi in Shelter Island Heights. Enjoy a tailored experience with all the comforts you desire.
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.
Quick stats about holiday rentals in Shelter Island Heights

Total holiday rentals
Explore 430 holiday rentals in Shelter Island Heights

Nightly prices starting at
Shelter Island Heights holiday rentals start at £60 per night before taxes and fees

Verified guest reviews
Over 16,450 verified reviews to help you choose

Family-friendly holiday rentals
350 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 140 rentals that welcome pets

Holiday rentals with a pool
160 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wifi availability
410 of Shelter Island Heights holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Shelter Island Heights rentals

4.9 Average rating
Shelter Island Heights stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with pools Shelter Island Heights
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- Yale University
- Foxwoods Resort Casino
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- Charlestown Beach
- Cooper's Beach, Southampton
- Southampton Beach
- Ocean Beach Park
- Mohegan Sun
- Sunken Meadow State Park
- East Matunuck State Beach
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- Long Island Aquarium
- Mount Southington Ski Area
- Mystic Seaport Museum
- Yale University Art Gallery
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