Showing 174 Vacation Rentals from Shelter Island, NY

Amenities:
No Pets, Non-Smoking, Outdoor Shower

Activities:
Beach, Biking, Yoga

Vacation Home Description:
description:this recently renovated 1890 victorian - with exquisite attention to detail and fixtures - is located in the historic district of shelter island heights. within walking distance to the north ferry (and greenport, with train/bus service to nyc) and the town of shelter island heights, this summer home features a wide wrap-around front porch with breezes and water view, and comes with membership to the heights beach club, a five minute walk. with two en-suite master bedrooms, a second floor single bedroom, and a third floor bonus/away/yoga/bedroom, the house is open, airy, clean, and spacious, blending indoor and outdoor spaces. though it's appearance may have a somewhat formal feel, past guests have consistently remarked about how comfortable, relaxed and easy the house is, with a very good 'vibe'. the first floor features a bay-windowed living room opening onto the front porch on one side and dining room on the other. the large, open and airy chef's kitchen with miele appliances, works great for multiple cooks and opens onto a sunny back porch and yard - complete with an antique glider for lazy afternoon naps! there is a hot/cold outdoor shower for rinses after the beach or evening bathing under the stars. the house comes with 3 bicycles, beach chairs, coolers and umbrella. the use of a jeep wrangler convertible is available for an additional fee (this vehicle is already registered for parking at island beaches). for extended stays, cleaning service can be arranged. this house was designed with relaxation, comfort and ease in mind. in the words of a past guest 'it feels like we were staying at a five star hotel and spa'.

Amenities:
BBQ, DVD Player, Fireplace, Internet Access, Linens, Non-Smoking, Pets OK, Stereo, Swimming Pool, TV, VCR

Activities:
Beach, Biking, Canoeing, Golf, Restaurants, Tennis

Vacation Home Description:
description:Looking for a great summer retreat' Restaurants, antiquing, wineries, biking, canoeing, tennis, golf and of course the beach are all yours to be had at this charming east end gem on laid back Shelter Island. The newly renovated Country Cape is nestled on a spacious and lush acre wooded lot. Located just 3 blocks from infamous Sunset Beach, the house sleeps 6, with 3 roomy, light filled bedrooms, 2 fully renovated tile/marble baths, newly remodeled eat in kitchen, formal dining room with big oak table that's great for entertaining, and a wood burning fireplace. Brand new heated gunite pool. Private, and beautifully landscaped two level 20x30 ft mahogany deck gets all day sun and is great for dinner parties or watching the kids play in the back yard while you're sipping a cocktail. House comes with bedroom ACs, fully outfitted kitchen, Weber charcoal BBQ, all linens, broadband internet/cable/ DVD/VCR/stereo, and a brand new 40 flat screen TV located above the fireplace. Please contact for more info/additional photos and pricing.

Amenities:
Jacuzzi, Lounge, Non-Smoking, Pets OK, Swimming Pool

Activities:
Beach

Vacation Home Description:
description:Located across street from waterfront, Our new Beach Vacation Home Rental is on the exclusive Shelter Island, The Jewel of The Hampton's in the Estate Section. European Elegance and influence abounds in this custom Vacation Home rental. Three Master Bedrooms plus Loft area sleeps 8 comfortably. The Bathrooms are En-Suite with twin pedestal sinks, Jacuzzi tubs, and separate showers. Showcased on the property is a beautiful in-ground 20'x40' Pool. Located across from Spectacular Waterfront Beach, Piers and Boat Launch. Designed and built by the editor of International travel publication our spectacular 3 bedrooms, 3 bath plus loft home is perfect for entertaining and enjoying the pool, waterfront beach and splendid landscaping. Two of Bedrooms have vaulted ceiling with skylights over the beds, imagine stargazing at night! These are designed in a Euro style and are en-suite with large jetted heated Jacuzzi tubs, twin pedestal sinks, huge tiled showers and separate pocket door with enclosed water closets. The third huge bedroom is located up a spiral staircase with a separate bath. Enjoy the Island via Skylights above, a sliding wood and glass door leads o your private deck with water views and the sound of waves lulling you to sleep. The expansive room includes a desk and work area for those type A personalities. Upstairs also includes a fabulous open music room/reading room with a couch bed. There are more skylights and many windows, bathing the level and home with an abundance of natural light. The main levels 35' soaring vaulted ceilings adds to the spacious feeling, the Great Room is very bright, showcased by natural light from the many skylights, myriad windows and multiple sets of French doors. The French doors open from the Living room, Great room and Kitchen to the grand covered 70 foot L shaped wrap-around covered porch with multiple sitting areas, lounge couch dinning table, and wine drinking spot.. The porch contains a gazebo area with dining table and mood lighting and overlooks both the beaut...

Amenities:
Dishwasher, Fireplace, Full kitchen, Non-Smoking, Outdoor Shower, Pets OK, Swimming Pool

Activities:
Beach, Yoga

Vacation Home Description:
description:A Very Romantic Getaway Vacation Cottage Home Rental in the Estate Section of Shelter Island (built 2002). Available Seasonally as well, please contact us for your desired dates. Seclusion, Water- Falls, Ponds, Step into the 2 Dipping Pools from House. Just across street from Waterfront, Beach and Boat Launch and Yacht dockage. This Shelter Island Hamptons Long Island NY is quite possibly the most Romantic Hideaway Vacation Rental available in the Hampton's NY area. Directly across the street from the waterfront, the sound and smells of water abound. Relax while you are surrounded by the myriad sounds of all our water features including, multiple waterfalls, fountains, pools and the waves. A waterfall in each of the 2 dipping pools located directly outside the 3 sided - sliding glass doors that create this amazing Zen-Like open-air room. There is a natural rock waterfall and multiple fountains in the large pond as well as another waterfall at the end of the driveway. Completing the water features a beautiful tiled large outdoor shower area. The Hamptons Shelter Island vacation hideaway is very secluded and was designed and built by an international travel editor to bestow the feeling and essence of being at a secluded European hideaway. The Tea House (as we call it) includes two floors of blissful living, each with it's own 2 sided gas fireplace. Ceramic tiles covers the floors extending outside the open-air room to the hand laid bluestone covered meditation/relaxation area. A full kitchen with dishwasher and glass breakfast area overlooks the pond and dipping pools and waterfalls. Seeking peace? The Beach Vacation Cottage is serenely peaceful - perfect for romance, writer or artists inspiration, inspiration, yoga and meditation, or simply complete relaxation. With it 's peaceful outdoor space you will truly be transported. Sit back and enjoy, the large pond with frogs and dozens of species of birds transcends the entire property with trickling stone waterfall. Sit, talk, listen to music, re...

Amenities:
Non-Smoking, Pets OK, Swimming Pool

Activities:
Beach

Vacation Home Description:
description:Enjoy this 4 Bedroom, 3 bath, with a 20 x 40 heated pool on privately landscaped tranquil acre within a short stroll to beaches.

Amenities:
Swimming Pool

Activities:
Golf, Tennis

Vacation rental Description:
description:with 4 bedrooms, 2 baths and deck surrounding a very secluded pool. Tucked away in the Heights near the golf course its close to everything and yet quiet and private. A wonderful l

Amenities:
Fireplace

Activities:
Tennis

Vacation rental Description:
description:with breakfast counter. Asking $1400. per month for winter. Walk to tennis, ferry, shops, dining and

Amenities:
Swimming Pool

Activities:
Restaurants, Tennis

Vacation rental Description:
description:SHELTER ISLAND CLOSE TO TOWN WITH POOL!

Amenities:
Pool Table

Activities:
Beach, Tennis

Vacation rental Description:
description:On a private drive with 2 bedrooms and bath upstairs, and guest room on main floor, open floor plan with living and dining room with door to deck, brand new kitchen. Wonderful master suite with new bathroom. Private dining deck and finished basement with pool table. Walk to sandy beach. July 12,000.

Amenities:
Garage

Activities:
Beach, Restaurants, Tennis

Vacation Home Description:
description:This newly renovated Beach House has charm, privacy and a separate guest suite above the garage. With 4 bedrooms, 2.5 baths and an open floor plan it's perfect for those who wish a getaway within walking distance to Beach, Ferries and Restaurants, quiet street, new furnishings, appliances and decks overlooking garden for relaxing. July $8,000. and August-LD $10,000.

Amenities:
-

Activities:
Restaurants, Tennis

Vacation rental Description:
description:SHELTER ISLAND HEIGHTS WALK TO NORTH FERRY

Amenities:
Air Conditioning, Alarm Clock, Fireplace, Hot Tub, Ironing Board, Jacuzzi, Microwave, No Pets, Non-Smoking, Phone, Refrigerator, TV

Activities:
Beach, Biking, Bird watching, Historical Sites, Kayaking, Massage, Shopping, Sightseeing, Swimming

Vacation Bed & Breakfast Description:
description:Welcome to the Candlelite Inn, Located on Beautiful Shelter Island, NY. The Candlelite Inn is a 175 year old Victorian, situated on one and a half acres in the center of Shelter Island. Recently renovated, The Candlelite Inn has 5 guestrooms with private baths, central air conditioning, television in the common living room and offers a continental breakfast. All rooms have a queen size bed and antique furniture. We have a beautiful wraparound porch to enjoy your morning coffee or just to relax at the end...

Amenities:
-

Activities:
Beach, Tennis

Vacation rental Description:
description:SHELTER ISLAND STEPS TO WADES BEACH

Amenities:
-

Activities:
Beach, Tennis

Vacation Home Description:
description:With a landscaped garden, cooks kitchen, dining porch with awning, spacious dining room, living room off the charming covered porch, this 3 bedroom, 2 bath cottage that is close to town and beach is a wonderful choice for your holiday. There is also a separate studio. $10,500.00 Aug-LD.

Amenities:
-

Activities:
Beach, Tennis

Vacation Home Description:
description:Steps from private beach this 3 bedroom, 2 baths beach house with waterview deck is great for summer fun. Winter Rental $1,500 monthly--flexible. August $12,000.