Shelter Island Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Shelter Island vacation rentals
1-bedroom cottage with Grove Beach 🏖️ access.
1-bedroom cottage with Grove Beach 🏖️ access.Clinton
9.6 out of 10, Exceptional, (46 reviews)
"We enjoyed our stay"
JM B.
The price is ￥25,037
￥44,619 total
includes taxes & fees
Jul 1 - Jul 2
9.2 out of 10, Wonderful, (25 reviews)
"Great stay & great staff!"
James
The price is ￥55,443
￥63,344 total
includes taxes & fees
Jul 12 - Jul 13
Rogers Lake House (87) · CT College+Beach+USCGA
Rogers Lake House (87) · CT College+Beach+USCGAOld Lyme
10.0 out of 10, Exceptional, (8 reviews)
The price is ￥23,554
￥77,402 total
includes taxes & fees
Jun 28 - Jun 29
Seabreeze #3 Cozy Cottage steps to the beach
Seabreeze #3 Cozy Cottage steps to the beachHampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is ￥13,910
￥74,451 total
includes taxes & fees
Jun 28 - Jun 29
Adorable Cottage, 5 min walk to water & town
Adorable Cottage, 5 min walk to water & townWestbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
Donovan V.
The price is ￥32,364
￥73,207 total
includes taxes & fees
Jun 28 - Jun 29
The Beach Nest-Lux Cottage Steps to the Beach
The Beach Nest-Lux Cottage Steps to the BeachClinton
9.8 out of 10, Exceptional, (6 reviews)
"This is exactly what we needed. Nice area, great place to walk, easy to relax. "
Karol W.
BlackBerry Private home with jacuzzi yearlong
BlackBerry Private home with jacuzzi yearlongEast Hampton
9.2 out of 10, Wonderful, (5 reviews)
"We had a great time staying here. The home is well worn and there are some fixtures that should be replaced "
Suzanne R.
The price is ￥18,277
￥164,393 total
includes taxes & fees
Jun 28 - Jun 29
The Stern at Soundview · Beach+Ocean+Sunrise
The Stern at Soundview · Beach+Ocean+SunriseOld Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
Lylian
The price is ￥26,265
￥49,535 total
includes taxes & fees
Jun 30 - Jul 1
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.
Find vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Shelter Island Hotel Reviews
The Shoals Suites and Slips
10/10 Excellent
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:
- View our selection of featured holiday rentals in Shelter Island
- Use the map to find apartments and other holiday homes in the Shelter Island neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Shelter Island while they last
Look no further and take a look at our great range of rental properties in Shelter Island!
Explore a world of travel with Expedia
- Luxury Hotels in Montauk
- Hostels in Montauk
- Hotels near Ponquogue Beach
- Cheap Hotels in Laurel
- Cheap Hotels in South Fork
- Vacation Homes in East Hampton
- Historic Hotels in Montauk
- Aparthotels in Noyack
- Hotels near Kirk Park Beach
- Luxury Hotels in Flanders
- Beach Hotels in Westhampton Beach
- Remsenburg Hotels
- Villas in Shelter Island
- Hotels near East Hampton Main Beach
- Holiday Park Resorts in Montauk
- Resorts in Riverside
- Cheap Hotels in Hamptons
- Aparthotels in Hamptons
- Resorts in Ridge
- Aparthotels in Amagansett
- Hotels near Montauk Downs State Park Golf Course
- Resorts in Springs
- Cheap Hotels in Suffolk County
- Silver Beach Hotels
- Motels in Wading River
- Aparthotels in Laurel
- Residences in Shinnecock Reservation
- Cheap Hotels in Montauk
- Resorts in Rocky Point
- Inns in Southampton
- Hotels with Hot Tubs in Montauk
- Boutique Hotels in Montauk
- Guest Houses in Village of East Hampton
- Riads in Fishers Island
- Winery Hotels in Riverhead
- Palaces in Southampton
- Hotels with Hot Tubs in Shelter Island
- Hotels near Riverhead Station
- Residences in Greenport
- Southampton Hotels
- Beach Hotels in Hamptons
- Motels in Riverhead
- Riverside Hotels
- Cheap Hotels in Peconic
- Beach Hotels in Beach Hampton
- Hostels in Shinnecock Reservation
- Chalets in South Jamesport
- Orient Point Hotels
- Vacation Homes in Hamptons
- Residences in Sagaponack
- Resorts in Shelter Island
- B&B in Southampton
- Rv Parks in North Fork
- Hotels near Cooper's Beach
- B&B in Montauk
- Luxury Hotels in Lion Head Beach
- Flanders Hotels
- Hotels near The Hamptons Beaches
- Boutique Hotels in Sag Harbor
- Inns in Village of Southampton
- Town Houses in Sag Harbor
- Cheap Hotels in East Hampton
- Resorts in Montauk
- Beach Hotels in Montauk
- Inns in Riverhead
- Boutique Hotels in Village of East Hampton
- Resorts in Westhampton Beach
- Vacation Homes in North Fork
- Cheap Hotels in Riverhead
- Town Houses in Montauk
- Castles in Southampton
- Inns in Bridgehampton
- Sag Harbor Hotels
- Vacation Homes in Westhampton Beach
- Town of Southampton Hotels
- Boutique Hotels in East Hampton
- Beach Hotels in Suffolk County
- East Hampton Hotels
- Montauk Hotels
- Cheap Hotels in North Fork
- Hotels with a Pool in Shelter Island
- Amagansett Hotels
- Resorts in Orient
- Resorts in Noyack
- Vacation Homes in Baiting Hollow
- Villas in Hamptons
- Inns in Sagaponack
- Houseboats in Springs
- Beach Hotels in East Hampton North
- Motels in Southold
- Apartments in Speonk
- All-Inclusive Hotel Hotels in Montauk
- Hotels near Brookhaven National Laboratory
