Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Shelter Island vacation rentals

Fridge, microwave, oven, stovetop

Work and Play Special! Extended Stay Discount

Work and Play Special! Extended Stay Discount
Shelter Island
10.0 out of 10, Exceptional, (53 reviews)
"This place is a perfect oasis in an already special environment. The host was wonderful and thoughtful. The cottage was magical and had everything to offer that one could want. "
United States
Adam M.
The price is ￥114,674
￥211,991 total
includes taxes & fees
Apr 13 - Apr 14
Work and Play Special! Extended Stay Discount
Interior

Floating Nest on Private River. Serene Views & Ultimate Relaxation

Floating Nest on Private River. Serene Views & Ultimate Relaxation
Old Lyme
The price is ￥35,836
￥59,806 total
includes taxes & fees
Apr 13 - Apr 14
Floating Nest on Private River. Serene Views & Ultimate Relaxation
Interior

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford
10.0 out of 10, Exceptional, (21 reviews)
"The home was exactly as described and well appointed, yet charming and cozy. Great location near Niantic, Stonington and Mystic. Perfect for a sister’s birthday getaway. "
United States
Dianne B.
The price is ￥27,872
￥56,740 total
includes taxes & fees
Apr 23 - Apr 24
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Cottage, 2 Bedrooms, Patio | Free WiFi, bed sheets

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is ￥28,143
￥32,153 total
includes taxes & fees
Apr 26 - Apr 27
North Fork Cottages & RV Resort
Beach nearby

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is ￥18,474
￥38,880 total
includes taxes & fees
Apr 13 - Apr 14
The Stern at Soundview · Beach+Ocean+Sunrise
1 bedroom, desk, iron/ironing board, travel crib

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (40 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is ￥13,188
￥29,158 total
includes taxes & fees
Apr 23 - Apr 24
1-bedroom cottage with Grove Beach 🏖️ access.
Beach nearby

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (4 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is ￥25,042
￥66,232 total
includes taxes & fees
Apr 13 - Apr 14
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Smart TV, books

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is ￥19,499
￥71,192 total
includes taxes & fees
Apr 15 - Apr 16
Rogers Lake House (87) · CT College+Beach+USCGA
Beach nearby

Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (54 reviews)
"Adorable cottage. Nice location. "
United States
Janet B.
The price is ￥17,918
￥43,199 total
includes taxes & fees
Apr 26 - Apr 27
Insta-worthy Couples Retreat: Perfect for romantic getaway!
Smart TV, fireplace, books

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Waterford
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful home, we enjoyed our stay. Clean, modern and had everything there we needed. Host was very attentive to our needs and was quick to respond. Looking forward to spend another long weekend there. Highly recommend!"
United States
Brenda W.
The price is ￥33,047
￥80,658 total
includes taxes & fees
May 12 - May 13
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (310 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is ￥23,609
￥31,305 total
includes taxes & fees
Apr 14 - Apr 15
Windward Shores Ocean Resort
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
The price is ￥24,905
￥35,375 total
includes taxes & fees
May 3 - May 4
Cliffside Resort Condominiums
Smart TV

Seabreeze 3 Cozy cottage by the beach

Seabreeze 3 Cozy cottage by the beach
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is ￥16,564
￥77,615 total
includes taxes & fees
Apr 13 - Apr 14
Seabreeze 3 Cozy cottage by the beach
1 bedroom, free WiFi, bed sheets

Hamptons apartment getaway

Hamptons apartment getaway
East Quogue
6.0 out of 10, (3 reviews)
"The room was a lot more spacious than I anticipated and everything was very clean. There was some music playing upstairs but it was quiet by nighttime. Check in and check out was very straightforward. Turning into the driveway was a bit difficult when the highway was crowded but was otherwise easy to find "
United States
Hilary K.
The price is ￥23,891
￥46,765 total
includes taxes & fees
Apr 13 - Apr 14
Hamptons apartment getaway
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥21,199
￥78,731 total
includes taxes & fees
Apr 14 - Apr 15
Beachside Bliss w/ Game Room, Gym & Golf Green
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,321 reviews)
"Great property "
United States
brian
Montauk Manor
Outdoor dining

Coastal New England Waterfront Home, Harkness Park, Casinos

Coastal New England Waterfront Home, Harkness Park, Casinos
Waterford
10.0 out of 10, Exceptional, (126 reviews)
"Great property!"
United States
Matthew B.
The price is ￥52,559
￥98,907 total
includes taxes & fees
Apr 24 - Apr 25
Coastal New England Waterfront Home, Harkness Park, Casinos
Beach nearby

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Westbrook Center
The price is ￥25,864
￥66,218 total
includes taxes & fees
Apr 26 - Apr 27
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Beach nearby

Freeboard at Soundview · Beach+Ocean+Sunrise

Freeboard at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.2 out of 10, Wonderful, (9 reviews)
"Great location and a nice room!"
United States
Angela M.
The price is ￥16,421
￥36,368 total
includes taxes & fees
Apr 13 - Apr 14
Freeboard at Soundview · Beach+Ocean+Sunrise
Beach nearby

The Anchor at Soundview · Beach+Ocean+Sunrise

The Anchor at Soundview · Beach+Ocean+Sunrise
Old Lyme
8.0 out of 10, Very Good, (2 reviews)
"So close to a peaceful lovely beach. Walking distance to food and even a synagogue!The bed was very comfortable and big. I enjoyed having coffee in my room before heading out to the beach. "
United States
October P.
The price is ￥16,421
￥36,368 total
includes taxes & fees
Apr 13 - Apr 14
The Anchor at Soundview · Beach+Ocean+Sunrise
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shelter Island Hotel Reviews

Sound View Greenport

Sound View Greenport

10/10 Excellent
"The staff was very friendly professional. Very engaging. The room was spotless and nice. it faced the Long Island sound breathtaking view are sliding glass door open up to a patio with steps that lead right to the beach ……. Stunning "
Diane 2-night trip
Posted 4 hours ago
Sound View Greenport

Find out more about Shelter Island

Search for holiday rentals in Shelter Island on Expedia! You can easily find your home rentals, villas, holiday apartments in Shelter Island using one of the methods below:

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Look no further and take a look at our great range of rental properties in Shelter Island!

Frequently asked questions

Can I find vacation rentals in Shelter Island?

Yes, we have vacation rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you'd like a relaxing place to stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area.

What are some of the best vacation home rentals that Shelter Island has to offer?

Unobstructed Ocean Views ! A Beautiful Montauk Getaway : This vacation home rental near Shelter Island is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Kick off your shoes and enjoy yourself with a patio and a garden.

How many vacation rentals are there in Shelter Island?

Choose from 86 Expedia vacation rentals in Shelter Island for a memorable vacation.

What can I see and do in Shelter Island?

Sunset Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Gardiner's Bay Country Club and Shelter Island Historical Society are other places to visit while you're in town.

What are vacation rentals like in Shelter Island?

Vacation rentals are private properties you can reserve for a couple days or more in Shelter Island. Vacation rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.