Vacation Rentals in Shelter Island Country Club, NY: Compare 10+ Sites & Save

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  5.  Shelter Island Heights
  6.  Shelter Island Country Club

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416 Best Vacation Rentals in Shelter Island Country Club (Starting from $118)

West Neck Guesthouse
West Neck Guesthouse
House
Shelter Island Heights, NY, USA
0.4k from Shelter Island Country Club center

Internet, View, Fireplace/Heating, Air Conditioner, Guest Services, Parking, Security/Safety

6 Bedrooms8 Guests
8.9

Fabulous

17 reviews

$358
Average price / night
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Spacious house next to the beach, Ferry and Eateries.
Spacious house next to the beach, Ferry and Eateries.
House
Shelter Island Heights, NY, 11965, United States
0.2k from Shelter Island Country Club center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet

6 Bedrooms11 Guests
10.0

Exceptional

4 reviews

$2343
Average price / night
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Modern on 9th
Modern on 9th
House
Greenport, NY, USA
2.4k from Shelter Island Country Club center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$403
Average price / night
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Relax and Enjoy!
Relax and Enjoy!
House
Shelter Island, NY, 11965, United States
0.3k from Shelter Island Country Club center

AC, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms10 Guests
10.0

Exceptional

16 reviews

$1958
Average price / night
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Sandpoint by Rove Travel Modern 5BR Family Home with Pool
Sandpoint by Rove Travel Modern 5BR Family Home with Pool
House
Shelter Island, NY, USA
2.5k from Shelter Island Country Club center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom12 Guests
New to Booking
$1760
Average price / night
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Shore House - A Luxury Beach Retreat
Shore House - A Luxury Beach Retreat
House
Shelter Island Heights, NY, 11965, United States
0.3k from Shelter Island Country Club center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$3370
Average price / night
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Cozy Greenport Cottage
Cozy Greenport Cottage
House
Greenport, NY, USA
2.9k from Shelter Island Country Club center

Accommodations, Pools, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms10 Guests
New to Booking
$559
Average price / night
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Kick back and unwind
Kick back and unwind
House
Shelter Island Heights, NY, 11965, United States
0.3k from Shelter Island Country Club center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

12 reviews

$556
Average price / night
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Bright Apartment - half Mi to Greenport Harbor!
Bright Apartment - half Mi to Greenport Harbor!
Apartment
Greenport, NY, USA
3.1k from Shelter Island Country Club center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom2 Guests
9.8

Exceptional

14 reviews

$236
Average price / night
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Relax By The Pool, Or Walk To The Beach And Restaurants
Relax By The Pool, Or Walk To The Beach And Restaurants
House
Shelter Island Heights, NY, 11965, United States
0.5k from Shelter Island Country Club center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$710
Average price / night
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Quaint DT Greenport Apt - 2 Mi to Shelter Island!
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
Apartment
Greenport, NY, USA
3.1k from Shelter Island Country Club center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom2 Guests
10.0

Exceptional

2 reviews

$208
Average price / night
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House on Chase Creek
House on Chase Creek
House
3 Locust Avenue, Shelter Island Heights, NY, 11965, United States
0.6k from Shelter Island Country Club center

AC, Free Parking, Frontdesk 24 Hour, Housekeeping, Internet, No Smoking, Outdoor Space

9.4

Superb

81 reviews

$140
Average price / night
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Charming Greenport Gem 1, 1 Mile to Ferry!
Charming Greenport Gem 1, 1 Mile to Ferry!
Apartment
Greenport, NY, USA
3.2k from Shelter Island Country Club center

Apartments, Cheap, Accommodations, Parking, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$118
Average price / night
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 Perfect Family Summer Vacation Home Close to beach 18x42 pool
Perfect Family Summer Vacation Home Close to beach 18x42 pool
House
Shelter Island, NY, 11964, United States
0.6k from Shelter Island Country Club center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
9.6

Exceptional

54 reviews

$756
Average price / night
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The Cliffside Resort Condominiums
The Cliffside Resort Condominiums
Apartment
Greenport, NY, USA
3.6k from Shelter Island Country Club center

Apartments, Cheap, Accommodations, Pools, Parking, 3-star, Lodgings, Vacation rentals, Beach

130 Bedrooms391 Guests
8.6

Fabulous

233 reviews

$405
Average price / night
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NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
House
Shelter Island, NY, 11965, United States
0.6k from Shelter Island Country Club center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
9.8

Exceptional

41 reviews

$504
Average price / night
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Beachfront Greenport Villa
Beachfront Greenport Villa
House
Greenport, NY, USA
3.9k from Shelter Island Country Club center

Air Conditioner, Barbecue/Outdoor Cooking, Parking, Internet, Security/Safety, Child Friendly

3 Bedrooms8 Guests
New to Booking
$913
Average price / night
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Newly renovated! Shelter Island Gem,  3 blocks from Sunset Beach
Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach
House
Shelter Island Heights, NY, 11968, United States
0.6k from Shelter Island Country Club center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.8

Exceptional

17 reviews

$1079
Average price / night
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Lavender Bay Breezes - Private Bay Beach Community
Lavender Bay Breezes - Private Bay Beach Community
House
Shelter Island Country Club, Shelter Island Heights, New York, USA
4.6k from Shelter Island Country Club center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Beach, Places to stay, Accessible hotels

4 Bedrooms8 Guests
New to Booking
$312
Average price / night
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Chic Shelter Island Home, Pool and Gardens
Chic Shelter Island Home, Pool and Gardens
House
Shelter Island, NY, 11965, United States
0.7k from Shelter Island Country Club center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$1754
Average price / night
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Hilltop Cottage Privacy Abounds
Hilltop Cottage Privacy Abounds
House
Shelter Island, NY, 11964, United States
0.7k from Shelter Island Country Club center

AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
7.4

Good

3 reviews

$599
Average price / night
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Very Large, Comfortable, Victorian 4 Bedroom House + Beach Club
Very Large, Comfortable, Victorian 4 Bedroom House + Beach Club
House
Shelter Island Heights, NY, 11965, United States
0.8k from Shelter Island Country Club center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms6 Guests
9.6

Exceptional

7 reviews

$1001
Average price / night
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Classic Waterview Victorian Summer Cottage in Park-Like-Setting
Classic Waterview Victorian Summer Cottage in Park-Like-Setting
House
Shelter Island Heights, NY, 11965, United States
0.8k from Shelter Island Country Club center

AC, Balcony, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

5 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$688
Average price / night
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Serene 3-bedroom house w/ Pool on Shelter Island
Serene 3-bedroom house w/ Pool on Shelter Island
House
Shelter island, NY, 11964, United States
1.0k from Shelter Island Country Club center

AC, Dryer, Heater, Internet, Laundry, Washer

New to Booking
$696
Average price / night
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Impeccably Restored & Charming Victorian Summer Cottage-5 Bed, 4 Bath, Sleeps 10
Impeccably Restored & Charming Victorian Summer Cottage-5 Bed, 4 Bath, Sleeps 10
House
Shelter Island Heights, NY, 11965, United States
1.0k from Shelter Island Country Club center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, No Smoking

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$1123
Average price / night
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Relaxing Shelter Island Getaway - great for families and couples!
Relaxing Shelter Island Getaway - great for families and couples!
House
Shelter Island Heights, NY, 11965, United States
1.1k from Shelter Island Country Club center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
9.8

Exceptional

43 reviews

$318
Average price / night
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Shelter Island 3 bed 2 1/2 bath, 1.3 acres private, quiet water view bay access.
Shelter Island 3 bed 2 1/2 bath, 1.3 acres private, quiet water view bay access.
House
Shelter Island, NY, 11964, United States
1.2k from Shelter Island Country Club center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$628
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Shelter Island Country Club.

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Frequently Asked Questions

You can explore 416 verified vacation rentals in Shelter Island Country Club. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Shelter Island Country Club vary depending on the season, property size, and location. Rates typically start from around $118 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Shelter Island Country Club include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Shelter Island Country Club welcome pets. Currently, 31 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Shelter Island Country Club often include amenities such as Fireplace/Heating, Laundry, and View. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.