Shelter Island Cottages
Get more for your budget and save up to 50% off select Secret Bargain hotels
Get even more value with CheapTickets Price Guarantee!
Change your flight without a fee on select flights
Cottages in Shelter Island

North Fork Resort
690 Queen St Greenport NY
$382 nightly
The price is $436 total per night
$436 total
Jun 22 - Jun 23
Total with taxes and fees
Located in Greenport, North Fork Resort is within a 5-minute drive of Kontokosta Winery and Stony Brook Eastern Long Island Hospital.
Pool
Pet friendly

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton CT
$220 nightly
The price is $249 total per night
$249 total
Jun 26 - Jun 27
Total with taxes and fees
With a stay at this cottage in Clinton, you'll be within a 10-minute drive of Hammonasset Beach State Park and Clinton Plaza Shopping Center.
Kitchen
Air conditioning

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
Waterford CT
$374 nightly
The price is $423 total per night
$423 total
Jun 21 - Jun 22
Total with taxes and fees
With a stay at this cottage in Waterford, you'll be within a 5-minute drive of Tumbleweeds and Childrens Museum of Southeastern Connecticut.
Kitchen
Washer

'The Gate House'on Beach front Estate with Dockage. Walk to Village .
greenport NY
Located in Greenport (Pipes Cove), this cottage is within a 15-minute walk of Railroad Museum of Long Island and East End Seaport Maritime Museum.
Kitchen
Washer

Fairy Tale Guest Cottage in Magic Garden by Pool
Bridgehampton NY
With a stay at this cottage in Bridgehampton, you'll be by the sea, within a 10-minute drive of The Hamptons Beaches and Children's Museum of The East End.
Pool
Free WiFi

Cozy cottage near downtown Clinton, Marina & Hammonasset Park
Clinton CT
With a stay at this cottage in Clinton, you'll be within a 5-minute drive of Hammonasset Beach State Park and Indian River Marina.
Kitchen
Washer

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook CT
$653 nightly
The price is $739 total per night
$739 total
Jun 21 - Jun 22
Total with taxes and fees
With a stay at this cottage in Old Saybrook (Old Saybrook Center), you'll be within a 10-minute walk of Fort Saybrook Monument Park and Connecticut River.
Kitchen
Washer

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton CT
With a stay at this cottage in Clinton, you'll be within a 10-minute drive of Hammonasset Beach State Park and Adam Stanton House and General Store Museum.
Kitchen
Dryer

Enchanted Waterfront Cottage
Old Lyme CT
Located in Old Lyme, this cottage is on a lake, within a 5-minute drive of Beckett Hill State Park and Florence Griswold Museum.
Kitchen
Pet friendly

NEW Coastal Cottage 2 Miles to Beach + Lake Access
Clinton CT
With a stay at this vacation home in Clinton, you'll be within a 5-minute drive of Hammonasset Beach State Park and Chamard Vineyards.
Washer
Dryer
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.
Shelter Island Cottages essential information
Accommodation | 227 Cottages |
|---|---|
Lowest Price | $249 |
Highest Price | $739 |
Popular accommodation | North Fork Resort, 1-bedroom cottage with Grove Beach 🏖️ access., Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk, 'The Gate House'on Beach front Estate with Dockage. Walk to Village ., Fairy Tale Guest Cottage in Magic Garden by Pool, Cozy cottage near downtown Clinton, Marina & Hammonasset Park, Driftwood Cottage @ Saybrook Point Marina, 2 King Beds, The gardners Cottage 1 mile from long Island Sound - pet friendly, Enchanted Waterfront Cottage, NEW Coastal Cottage 2 Miles to Beach + Lake Access, Cozy & Warm Getaway Cottage in Beach Community, Cozy cottage on Fort Pond Lake. |
More to Explore in Shelter Island
Top Picks
- Spa Resorts & in Greenport
- Hotels near Lenz Winery
- 3 Star Hotels in Bridgehampton
- Hotels with Shopping in Bridgehampton
- Business Hotels in Bridgehampton
- 3 Star Hotels in Mattituck
- Lodges in Mattituck
- Lodges in North Fork
- Greenport Hotels
- Guest Houses in Jamesport
- 4 Star Hotels in Greenport
- Hotels with Free Breakfast in Greenport
- Cottages in North Fork
- Hotels with Air Conditioning in Sag Harbor
- Winery Hotels in Greenport
- Motels in Shelter Island
- Hotels near Sparkling Pointe
- Chalets in Shelter Island
- Hotels with Free Breakfast in Bridgehampton
- Hotels near Pindar Vineyards
- Condo Rentals in Southampton
- 5 Star Hotels in Greenport
- Villas in Water Mill
- Apartments in Sag Harbor
- Hotels with Bars in Sag Harbor
- Beach Resorts & in Sag Harbor
- Hotels with Shopping in Sag Harbor
- 5 Star Hotels in Bridgehampton
- Adventure Sport Hotels in Shelter Island
- Hotels with Kitchenettes in Southold
- Southold Hotels
- Hotels near Bedell Cellars
- 4 Star Hotels in Bridgehampton
- Hotels with Free Parking in Bridgehampton
- 5 Star Hotels in Shelter Island
- 3 Star Hotels in Southold
- Motels in Sag Harbor
- Cabin Rentals in Shelter Island
- Pet Friendly Hotels in Sag Harbor
- Hotels with WiFi in Southold
- Clearwater Beach Hotels
- Hotels with Pools in Sag Harbor
- Farmstay in Amagansett
- Hotels with an Indoor Pool in Sag Harbor
- Hostels in Mattituck
- Hotels near Orient Point County Park
- Winery Hotels in Sag Harbor
- Extended Stay Hotels in Southold
- Oceanfront Hotels in Greenport
- Hotels near East Hampton
- Extended Stay Hotels in Amagansett
- Condo Rentals in Bridgehampton
- Chalets in Southampton
- Chalets in Sagaponack
- Hotels with Free Breakfast in Southold
- Extended Stay Hotels in Greenport
- Golf Resorts & in Sag Harbor
- Lodges in Southampton
- Water Mill Hotels
- Silver Beach Hotels
- Cabin Rentals in Sag Harbor
- Motels in North Fork
- Hotels near Orient Beach State Park
- Arcade Hotels in Amagansett
- Condo Rentals in Shelter Island
- Shelter Island Heights Hotels
- Boutique Hotels in Greenport
- Town of Southold Town Hotels
- Chalets in Water Mill
- Coecles Harbor Hotels
- Hotels with a Gym in Bridgehampton
- Lafarges Landing Hotels
- 5 Star Hotels in Southold
- Lodges in Southold
- 4 Star Hotels in Sagaponack
- 5 Star Hotels in Sag Harbor
- Villas in Mattituck
- Inns in Shelter Island
- Hotels with Pools in Southold
- 3 Star Hotels in Sag Harbor
- Hotels with a Gym in Sag Harbor
- 4 Star Hotels in Southold
- Hotels with a Wedding Venue in Bridgehampton
- Hotels with Pools in Bridgehampton
- Extended Stay Hotels in Southampton
- Lodges in Jamesport
- 4 Star Hotels in Sag Harbor
- Hotels with Air Conditioning in Southold
- 5 Star Hotels in Water Mill
- Condo Resorts in Shelter Island
- Hotels with Restaurants in Southold


