
Holiday houses in Shelter Island
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Top-rated holiday rentals in Shelter Island
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!

2 BR Waterfront Escape in Wine Country
Overlooking the Long Island Sound, this oceanfront condo is the ultimate escape. Bask in the sun on a private beach or unwind on the waterfront deck with breathtaking views Minutes from the town center, you’ll find local farms, award-winning wineries, gourmet restaurants & charming shops ⚓️ Explore Greenport: A historic seaport with coastal charm & rich culture 🏖 Premium Amenities – Waterfront deck, private balcony, grills, pool, private beach & parking ⛴ Ferry Access to Shelter Island & CT

Shelter Island family getaway steps from beaches
Just 2 blocks from Hay Beach, our family & pet-friendly 3BR home offers space to relax & play. Enjoy a large yard w/ fire pits, beach gear, games, & toddler toys. Inside: open living area, fireplace, full kitchen, 2 baths, playroom, workout space, & extra sleeping options. Quiet neighborhood, perfect for families. Winter stays: cozy up by the fire & enjoy $0 cleaning fee Nov–Mar. Host lives next door for quick support. For the littles there is a full sized crib high chair and bathtub.

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

Beautiful beach home with pool & water views!
Perfectly situated just past the Island Boatyard and Salt in a blissful neighborhood surrounded by water on 3 sides. 4 town landings and beach access right across the street. Newly renovated gourmet kitchen with large island and beautiful quartz counters. Back deck offers full outdoor dining space with propane Weber grill, wicker seating area with beautiful propane Firepit for hours of evening enjoyment and chaise lounges by the pool.

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!

Recharge at our Renovated ocean front unit
Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.

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.

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

Walk to Breakwater Beach in Heart of Wine Country
Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.
Popular amenities for Shelter Island holiday rentals
Stay near Shelter Island's top sights
Other great holiday rentals in Shelter Island

Hamptons Tiny House!

Family Friendly Island Home

Huge Island Getaway Pool HotTub Walk To Beach

Cosy North Fork Cottage with large backyard

Stylish Studio Suite on Shelter Island

Cozy Shelter Island 2 Bedroom 1 Bath Cottage

Nassau Point, North Fork Home w/ Pool

Waterfront Condo C-204 at The Cliffside Resort
When is the best time to visit Shelter Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $501 AUD | $501 AUD | $702 AUD | $527 AUD | $808 AUD | $843 AUD | $940 AUD | $945 AUD | $808 AUD | $632 AUD | $702 AUD | $667 AUD |
| 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
Where should I stay in Shelter Island?
Make yourself at home in Shelter Island by choosing from our most frequently booked neighborhoods. We have over 1,630 vacation rentals in Shelter Island, and over 1,570 vacation rentals in North Haven.
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 70 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 60 vacation homes with pools in Shelter Island, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly house rentals in Shelter Island?
Shelter Island has more than 100 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in bed and breakfast rentals in Shelter Island?
Experience the best of Shelter Island with our bed and breakfast rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Shelter Island have air conditioning?
Absolutely! We offer over 100 house rentals with air conditioning 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 110 house rentals with wifi in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Shelter Island have a bbq area?
Absolutely! We offer over 60 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 a gym?
Absolutely! We offer over 20 house rentals with a gym in Shelter Island. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Shelter Island

Total holiday rentals
Explore 150 holiday rentals in Shelter Island

Nightly prices starting at
Shelter Island holiday rentals start at $14 AUD per night before taxes and fees

Verified guest reviews
Over 3,210 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
140 of Shelter Island holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Shelter Island rentals

4.9 Average rating
Shelter Island stays are highly rated by guests—averaging 4.9 out of 5!
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- Family-friendly rentals Shelter Island
- House rentals Shelter Island
- Rentals with a patio Shelter Island
- Beachfront rentals Shelter Island
- Rentals with outdoor seating Shelter Island
- Rentals with a washing machine and dryer Shelter Island
- Rentals with a kayak Shelter Island
- Rentals with a hot tub Shelter Island
- Rentals with a fire pit Shelter Island
- Rentals with beach access Shelter Island
- Fitness-friendly rentals Shelter Island
- Rentals with pools Shelter Island
- Rentals with a fireplace Shelter Island
- Waterfront rentals Shelter Island
- Pet-friendly rentals Shelter Island
- Yale University
- Foxwoods Resort Casino
- Fairfield Beach
- Charlestown Beach
- Cooper's Beach, Southampton
- Southampton Beach
- Ocean Beach Park
- Mohegan Sun
- Sunken Meadow State Park
- East Matunuck State Beach
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Long Island Aquarium
- Mount Southington Ski Area
- Mystic Seaport Museum
- Yale University Art Gallery
- Burlingame State Park
- Sleeping Giant State Park
- Orient Beach State Park
- East Hampton Main Beach
- Meschutt Beach
- Point Judith Lighthouse
- Wölffer Estate Vineyard
- Ditch Plains Beach




