Shelter Island Luxury Vacation Rentals
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Great deal
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Beach access
Shelter Island Retreat W/ Outdoor Pool!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Fitness centre
- Outdoor swimming pool
Shelter Island Retreat W/ Outdoor Pool!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Fitness centre
- Outdoor swimming pool
Shelter Island Retreat W/ Outdoor Pool!
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Top location
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Beach access
Sandpoint By Rove Travel - 6Br Family Home With Pool
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Outdoor swimming pool
Sandpoint By Rove Travel - 6Br Family Home With Pool
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Outdoor swimming pool
Sandpoint By Rove Travel - 6Br Family Home With Pool
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Best-rated
King-Bed Room With Private Bath -Free Wifi-- New London-Mystic
- Shared kitchen
- Free parking
- VIP check-in/ -out
- Air conditioning
- Tea and coffee facilities
- Heating
King-Bed Room With Private Bath -Free Wifi-- New London-Mystic
- Shared kitchen
- Free parking
- VIP check-in/ -out
- Air conditioning
- Tea and coffee facilities
- Heating
King-Bed Room With Private Bath -Free Wifi-- New London-Mystic
Cheap Vacation Rentals in Shelter Island New York State
Fancy Studio Private Entrance
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
- Patio
Fancy Studio Private Entrance
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
- Patio
Fancy Studio Private Entrance
Riverside Retreat-Waterfront Walkout Apartment
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Terrace
Riverside Retreat-Waterfront Walkout Apartment
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Terrace
Riverside Retreat-Waterfront Walkout Apartment
Luxury Villa: Mohegan Retreat with Fireplace, Jacuzzi, and Pools
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sauna
- Saltwater pool
Luxury Villa: Mohegan Retreat with Fireplace, Jacuzzi, and Pools
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sauna
- Saltwater pool
Luxury Villa: Mohegan Retreat with Fireplace, Jacuzzi, and Pools
Pet Friendly Vacation Rentals Shelter Island
Downtown New Haven, Spacious Stay By Yale - Ao Destinations
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Car park
Charges may apply
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Heating
Downtown New Haven, Spacious Stay By Yale - Ao Destinations
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Car park
Charges may apply
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Heating
Downtown New Haven, Spacious Stay By Yale - Ao Destinations
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Beach access
The Pines Men-Only Stay
- VIP check-in/ -out
- Air conditioning
- Fitness centre
- Saltwater pool
- Heated swimming pool
- Outdoor swimming pool
The Pines Men-Only Stay
- VIP check-in/ -out
- Air conditioning
- Fitness centre
- Saltwater pool
- Heated swimming pool
- Outdoor swimming pool
The Pines Men-Only Stay
Villa Signor
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Steam room
- Outdoor swimming pool
Villa Signor
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Steam room
- Outdoor swimming pool
Villa Signor
Shelter Island Vacation Rentals Oceanfront
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Guest favorite
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Private beach
The Cliffside Resort Condominiums
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Laundry
- Outdoor swimming pool
The Cliffside Resort Condominiums
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Laundry
- Outdoor swimming pool
The Cliffside Resort Condominiums
Private Apt King Suite, L.I, Ny-Hamptons To Nyc
- Free parking
- Air conditioning
- Flat-screen TV
- Luggage storage
- Tea and coffee facilities
Private Apt King Suite, L.I, Ny-Hamptons To Nyc
- Free parking
- Air conditioning
- Flat-screen TV
- Luggage storage
- Tea and coffee facilities
Private Apt King Suite, L.I, Ny-Hamptons To Nyc
Historic Peaceful Apartment
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Skiing
- Garden area
Historic Peaceful Apartment
- Cookware/ Kitchen utensils
- Free parking
- Security
- Air conditioning
- Skiing
- Garden area
Historic Peaceful Apartment
Shelter Island Vacation Rentals with Private Pool
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Private beach
Cozy Garden Apartment Along The Shoreline
- BBQ facilities
- Free parking
- Express check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun loungers
Cozy Garden Apartment Along The Shoreline
- BBQ facilities
- Free parking
- Express check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun loungers
Cozy Garden Apartment Along The Shoreline
Hyatus Luxury Residences City Crossing
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Fitness centre
- Rooftop pool
Hyatus Luxury Residences City Crossing
- BBQ facilities
- Free parking
- 24-hour security
- Air conditioning
- Fitness centre
- Rooftop pool
Hyatus Luxury Residences City Crossing
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Beach access
Exceptional Contemporary Retreat With 4 King Beds In Mystic Ct
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun terrace
Exceptional Contemporary Retreat With 4 King Beds In Mystic Ct
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun terrace
Exceptional Contemporary Retreat With 4 King Beds In Mystic Ct
Private Guest House W/ Deck + Spectacular Views!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Heating
- Outdoor swimming pool
Private Guest House W/ Deck + Spectacular Views!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Heating
- Outdoor swimming pool
Private Guest House W/ Deck + Spectacular Views!
Mystic Refuge W/ Patio < 1 Mi To Downtown!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Terrace
Mystic Refuge W/ Patio < 1 Mi To Downtown!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Ironing facilities
- Terrace
Mystic Refuge W/ Patio < 1 Mi To Downtown!
Beautiful Studio Apartment In Historic House
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Beautiful Studio Apartment In Historic House
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Garden area
Beautiful Studio Apartment In Historic House
Casa Soleada In East Rock Near Dt And Yale Som With Free Parking And King Bed
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Laundry
Casa Soleada In East Rock Near Dt And Yale Som With Free Parking And King Bed
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Laundry
Casa Soleada In East Rock Near Dt And Yale Som With Free Parking And King Bed
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Beach access
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Luggage storage
- Garden area
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Luggage storage
- Garden area
Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Are you in a hurry?
Here is a quick list of Vacation Rentals in Shelter Island, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| King-Bed Room With Private Bath -Free Wifi-- New London-Mystic |
9.6 / 10 (115 Reviews) |
From 140$ | |
| Fancy Studio Private Entrance |
9.3 / 10 (72 Reviews) |
From 105$ | |
| Riverside Retreat-Waterfront Walkout Apartment |
9.5 / 10 (82 Reviews) |
From 286$ | |
| Luxury Villa: Mohegan Retreat with Fireplace, Jacuzzi, and Pools |
9.4 / 10 (63 Reviews) |
From 138$ | |
| Downtown New Haven, Spacious Stay By Yale - Ao Destinations |
8.8 / 10 (192 Reviews) |
From 117$ |
Frequently Asked Questions
What vacation rentals with pools are available in Shelter Island?
The Shelter Island Retreat offers an outdoor pool ideal for family gatherings and relaxation. Additionally, Mystic Refuge features a private patio with easy pool access for guests.
Consider visiting in the off-peak season to enjoy quieter poolside activities and lower rental rates, especially in early June.
Where can I find vacation rentals near the beach on Shelter Island?
Cozy Garden Apartment Along The Shoreline is just steps away from the beach. Riverside Retreat offers waterfront views and a short walk to sandy shores.
Head to the beach before 10am for the best sunlight and fewer crowds, perfect for family photos.
Which Shelter Island rentals are near local attractions?
Villa Signor is conveniently located near several local parks and dining options. You can explore the charm of the nearby historic district from the luxury of your accommodation.
Walk to the local farmers' market on Saturday mornings for fresh produce and local goods, located just a mile away from the villa.
What vacation rentals in Shelter Island are good for families?
Sandpoint by Rove Travel offers a spacious 6-bedroom home, perfect for large family gatherings. Its family-friendly amenities include a large outdoor area for kids to play.
Book your stay during the weekdays in August when rental prices drop slightly for a family-friendly experience without the weekend rush.
Which Shelter Island rentals offer stunning views?
The Private Guest House With Deck offers spectacular views of the bay. You can enjoy sunsets right from your own balcony for a memorable evening experience.
Pack a picnic and enjoy it on the deck around sunset for a picturesque dining experience.
Are there affordable vacation rentals for budget travelers in Shelter Island?
Private Apt King Suite, L.I, Ny-Hamptons To Nyc is an economical option for travelers looking to explore the area without breaking the bank. Gardner Lake also offers reasonably priced private accommodations.
Look for weekly rates if you plan a longer stay; it can save you more compared to nightly rates.
What unique activities are available near Shelter Island for vacation renters?
Explore nearby hiking trails at Mashomack Preserve or book a fishing trip with local charters. These activities allow guests to connect with nature and enjoy the scenic surroundings.
Arrange outdoor activities early in the morning for cooler temperatures and higher chances of seeing wildlife.
What are the best times to visit Shelter Island for vacation rentals?
Late spring, from late May to early June, and early fall, from September to mid-October, offer pleasant weather and fewer crowds. This is when rental prices can be lower, making it a budget-friendly choice.
Consider booking your rental in March for early rates, securing a better deal as summer approaches.
How should I plan meals while renting a vacation home on Shelter Island?
Many rentals like Cozy Garden Apartment provide kitchens for cooking. You can purchase groceries at local shops or visit nearby restaurants for fresh seafood.
Check local hours for farmers' markets, often open on weekends, for fresh, local ingredients to incorporate into your meals.
What should I know about parking when renting on Shelter Island?
Most vacation rentals like Casa Soleada provide free parking, allowing for easy travel. Street parking is also available in quieter areas, but be mindful of any local restrictions.
Arrive early to secure free parking spots during peak tourist hours, especially around popular dining areas.