
House holiday rentals in Shelter Island Heights
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Top-rated house rentals in Shelter Island Heights
Guests agree: these houses 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!

Summer Retreat at the beach , enjoy Wine Country
* We provide a Beach Parking Pass for all Southold Town Beaches * 10 min walk to neighborhood sandy beach! * 5 min walk to vineyard with tasting room. Spacious Contemporary home. Master Bedroom plus 2 more bedrooms and 2 bathrooms on the second floor. Living room & kitchen on main floor. Wake up to beautiful garden view. Large kitchen and dining area for the whole family. Just minutes from Long Island's wineries and wedding venues. This home comes complete with everything you need!

Designer's Dream - Charming Boathouse
An architect's and interior decorator's dream home! This home is a historic boathouse built in the late 1890's with modern updates. In the middle of Greenport Village - walking distance to train station, Jitney stop, and Shelter Island Ferry as well as the best North Fork restaurants, vineyards, bars, and beaches. Two bedroom home with ground floor fireplace, outdoor shower (not enclosed), and beautifully landscaped outside patio w/grilling & dining areas.

Hay Beach Family Home: Fire Pit, Playroom, Yard
Two blocks from Hay Beach, this family-and-dog-friendly 3BR sleeps 6 in a quiet Shelter Island neighborhood. Fenced yard, fire pit, playroom, crib, toddler toys, beach gear, and bikes included. The home was built for families: open living area with wood-burning fireplace, full kitchen, 2 full baths, basement playroom, and workout space. Outside: fully fenced yard, fire pit, sun loungers, propane grill, Big Green Egg. Winter stays: $0 cleaning fee Nov–Mar.

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!

The Cooper-Burke House
Many Main Street restaurants such as the American Hotel, Lulu's, Page 63, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.

Harbor Heights
100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly renovated 2-Family Home! This is for rental of 2nd floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

1830 Historic garden wing - walk to it all
This historic Captain's house is located in the heart of beautiful Greenport Village. It dates back to 1830 and has been beautifully renovated preserving its historic detail. It has a huge garden with mature trees, plants and a wonderful gazebo. Once you step outside, you can walk to all the restaurants, bars, shops, the water as well as the Hampton Jitney and the LIRR. It's an ideal yet very quaint location.

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.

Secluded Farmhouse - Studio Apartment Style Unit
Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.

Greenport Village walking distance to all
Large spacious home in the heart of wine country. Roomy den for relaxing after the wineries. Screened in patio for al fresco dining and enjoying the spacious yard. Hot tub operational year round! Strong, fast wifi with multiple extenders. Message me with any questions or for special offers on 4/5 day stays or midweek 2/3 night specials.

Nofo Bungalow-In The Heart of Greenport Village
This historic Greenport home has been completely renovated . The Bungalow is in the heart of Greenport Village on a quiet dead end. The home includes 1500 square feet of open concept living, two bedrooms, and two full baths. The downstairs bedroom features a queen and upstairs bedroom four twins.
Popular amenities for house rentals in Shelter Island Heights
House rentals with a pool

Private Oasis W/Stunning Vinyard and Pool Views

Private & Pristine with Pool and Kid’s Playard

4 Bedroom Sag Harbor Home w/ Pool & Tennis Access

The Perfect North Fork Escape

Casa Greenport

Stylish Beach Getaway: pool & walking location

Brand new house with an all year round hot tub.

East Hampton Oasis - Pool and Hot Tub
Weekly house rentals

Elegant Greenport Victorian-Winter Harbor House-

North Fork Waterfront Escape · Sunset Views

POOL + Beach Oasis! Winter deals 2+ nights!

Waterfront NoFo Cottage w/ public beach access

Greenport Village Relaxation

Sunlit cozy cottage by the bay.

Relaxing Spacious House. *pets welcomed*

The Olde Church in Greenport
Private house rentals

Greenport Getaway - North Fork Rental

Modern Farmhouse Oasis in GP Village

The Sandy Shack - Coastal Escape

Sweeping Dunes Beach Cottage

Luxe Southampton Home w/Pool 5 Min Walk to US Open

East end home away from home

Sag Harbor Village 3 Bedroom Gem

Walk to town, Greenport Village - Harbor Views
When is the best time to visit Shelter Island Heights?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $659 SGD | $642 SGD | $604 SGD | $638 SGD | $721 SGD | $829 SGD | $881 SGD | $900 SGD | $766 SGD | $651 SGD | $679 SGD | $702 SGD |
| 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 |
Quick stats about house rentals in Shelter Island Heights

Total holiday rentals
Explore 270 holiday rentals in Shelter Island Heights

Nightly prices starting at
Shelter Island Heights holiday rentals start at $166 SGD per night before taxes and fees

Verified guest reviews
Over 9,140 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 110 rentals that welcome pets

Holiday rentals with a pool
100 properties feature pools

Rentals with dedicated workspaces
150 properties have a dedicated workspace

Wifi availability
270 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 beach access Shelter Island Heights
- Family-friendly rentals Shelter Island Heights
- Rentals with pools Shelter Island Heights
- Rentals with a fireplace Shelter Island Heights
- Pet-friendly rentals Shelter Island Heights
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- Boutique hotels Shelter Island Heights
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- Beach
- Yale University
- Cooper's Beach, Southampton
- Fairfield Beach
- Charlestown Beach
- East Matunuck State Beach
- Mohegan Sun
- Ocean Beach Park
- Foxwoods Resort Casino
- Mystic Seaport Museum
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- Point Judith Lighthouse
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- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Long Island Aquarium
- Blue Shutters Beach
- Wölffer Estate Vineyard
- Mount Southington Ski Area
- Orient Beach State Park
- Ocean Beach
- Meschutt Beach
- Mystic Aquarium





