Book Bed and Breakfast in Shelter Island

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Featured B&B in Shelter Island

The Sagaponack

The Sagaponack

3 out of 5
3720 Montauk Hwy Wainscott NY
$421 nightly
The price is $473 total per night
$473 total
Sep 16 - Sep 17
Total with taxes and fees
Guests of The Sagaponack enjoy free WiFi in public areas, a seasonal outdoor pool, and a communal living room. If you drive, put free parking to good use. Front-desk staff can help with luggage storage, and provide local restaurant recommendations. Additional amenities include a water dispenser, a gift shop, and a porter/bellhop.
Pool
Pet friendly
Harpoon House

Harpoon House

3 out of 5
136 Main St Southampton NY
$305 nightly
The price is $348 total per night
$348 total
Sep 3 - Sep 4
Total with taxes and fees
Harpoon House features free WiFi in public areas, coffee in a common area, and a meeting room. If you decide to drive, there's free parking. The 24-hour front desk has staff standing by to help with dry cleaning/laundry and tours/tickets. Additional amenities include express check-in, express check-out, and a terrace.
Pet friendly
Parking included
Inn at Harbor Hill Marina

Inn at Harbor Hill Marina

3.5 out of 5
60 Grand St Niantic CT
$269 nightly
The price is $309 total per night
$309 total
Sep 1 - Sep 2
Total with taxes and fees
Guests of Inn at Harbor Hill Marina enjoy features like a marina, free WiFi in public areas, and meeting rooms. There's free parking if you drive. Front-desk staff can assist with luggage storage and tours/tickets. Other amenities at this beach bed & breakfast include conference space, a refrigerator in a common area, and free use of bicycles.
Breakfast included
Parking included
The Huntting Inn

The Huntting Inn

3.5 out of 5
94 Main St East Hampton NY
$612 nightly
The price is $698 total per night
$698 total
Sep 1 - Sep 2
Total with taxes and fees
The Huntting Inn features free WiFi in public areas, refrigerator in a common area, and a meeting room. If you decide to drive, there's free valet parking. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Additional amenities include a garden and a TV in a common area.
Breakfast included
Parking included
The Hedges Inn

The Hedges Inn

3.5 out of 5
74 James Lane East Hampton NY
$751 nightly
The price is $858 total per night
$858 total
Sep 13 - Sep 14
Total with taxes and fees
The Hedges Inn features free WiFi in public areas, meeting rooms, and coffee in a common area. Free valet parking is included with your stay. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and concierge services. Other amenities at this adults-only bed & breakfast include free use of bicycles, a computer station, and a library.
Breakfast included
Pet friendly
The Captain Stannard

The Captain Stannard

3 out of 5
138 South Main Street Westbrook CT
$219 nightly
The price is $243 total per night
$243 total
Aug 26 - Aug 27
Total with taxes and fees
Guests of The Captain Stannard enjoy free WiFi in public areas, refrigerator in a common area, and free use of bicycles. There's free parking and an airport shuttle for a fee. Additional amenities include express check-out, a terrace, and local meal delivery service.
Breakfast included
Parking included
Mill House Inn

Mill House Inn

5 out of 5
31 North Main Street East Hampton NY
$1,107 nightly
The price is $1,265 total per night
$1,265 total
Sep 7 - Sep 8
Total with taxes and fees
Guests of Mill House Inn enjoy free WiFi in public areas, meeting rooms, and a library. A stay here includes free parking. Front-desk staff can assist with luggage storage and tours/tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury bed & breakfast include express check-out, a terrace, and a picnic area.
Breakfast included
Pet friendly
Head of Pond House

Head of Pond House

3 out of 5
403 Head of Pond Rd Water Mill NY
$2,340 nightly
The price is $2,673 total per night
$2,673 total
Sep 9 - Sep 10
Total with taxes and fees
Guests of Head of Pond House enjoy access to free WiFi in public areas, a seasonal outdoor pool, and refrigerator in a common area. If you decide to drive, there's free parking. A multilingual staff is on hand to help with luggage storage, and offer sightseeing advice. Additional amenities include a terrace, a garden, and a communal living room.
Pool
Breakfast included
The Scranton Seahorse Inn

The Scranton Seahorse Inn

3 out of 5
818 Boston Post Road Madison CT
$299 nightly
The price is $332 total per night
$332 total
Sep 3 - Sep 4
Total with taxes and fees
The Scranton Seahorse Inn features free WiFi in public areas, refrigerator in a common area, and a meeting room. You can take advantage of free parking, along with an airport shuttle for a fee. Helpful staff can provide dry cleaning/laundry services and concierge services. Additional amenities include a library, express check-out, and a terrace.
Breakfast included
Pet friendly
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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.

Hotel Options in Shelter Island

    Pier Blue Inn Old Saybrook - Essex

    Pier Blue Inn Old Saybrook - Essex

    1430 Boston Post Rd Old Saybrook CT
    $96 nightly
    The price is $110 total per night from Sep 10 to Sep 11
    $110 total
    Sep 10 - Sep 11
    Total with taxes and fees
    Sound View Greenport

    Sound View Greenport

    58775 County Rd 48 Greenport NY
    $322 nightly
    The price is $368 total per night from Sep 9 to Sep 10
    $368 total
    Sep 9 - Sep 10
    Total with taxes and fees
    The Atlantic Hotel

    The Atlantic Hotel

    1655 County Road 39 Southampton NY
    $219 nightly
    The price is $250 total per night from Sep 8 to Sep 9
    $250 total
    Sep 8 - Sep 9
    Total with taxes and fees

Bed and Breakfast

Book a bed and breakfast in Shelter Island
A romantic getaway awaits when you book a bed and breakfast in Shelter Island. The beauty of renting a B&B is that each one is unique. A farm B&B is cozy and rustic, while a luxury B&B provides top-of-the-line luxuries, including in-room jet tubs and thousand thread-count sheets. And let’s not forget the most important part of its name…breakfast! Bed & breakfasts are famous for putting out a great spread each morning. Fill your plate with fluffy pancakes with maple syrup, hot eggs right from the pan, and a cup of hot coffee to help get you ready for the rest of your day.

All are welcome at Shelter Island bed n breakfasts
Some cheap accommodations are designed to simply give travelers a roof overhead and a comfortable bed to sleep on between adventures or business meetings. This definitely isn’t the case with a bed and breakfast (also known as a breakfast inn). The right B&B doesn’t just host your vacation to Shelter Island, it becomes part of it. In many cases, travelers get to know the manager of the B&B, as well as mingle with other guests. Many B&Bs also arrange activities for guests, such as hikes in the area, bird watching outings, or fun game nights. 

B&B hotels have a reputation as a romantic retreat for couples. However, B&Bs are actually for all sorts of travelers. Book one with a parent, child, or your favorite travel buddy. Want to take your fur child on your adventure to Shelter Island? A quick search through Orbitz will bring up pet-friendly B&B options so your best friend can come along.

Shelter Island B&B essential information

Accommodation
46 B&B
Lowest Price
$110
Highest Price
$2,673
Popular accommodation
The Sagaponack, Harpoon House, Inn at Harbor Hill Marina, The Huntting Inn, The Hedges Inn, The Captain Stannard, Mill House Inn, Head of Pond House , The Scranton Seahorse Inn

More to Explore