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
$205 nightly
The price is $234 total per night
$234 total
Oct 14 - Oct 15
Total with taxes and fees
Guests of The Sagaponack enjoy free WiFi in public areas, a seasonal outdoor pool, and a water dispenser. 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 communal living room, a gift shop, and a porter/bellhop.
Pool
Pet friendly
The Huntting Inn

The Huntting Inn

3.5 out of 5
94 Main St, East Hampton, NY
$393 nightly
The price is $447 total per night
$447 total
Nov 2 - Nov 3
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 TV in a common area and a garden.
Breakfast included
Parking included
Inn at Harbor Hill Marina

Inn at Harbor Hill Marina

3.5 out of 5
60 Grand St, Niantic, CT
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $194 total per night
$194 total
Nov 2 - Nov 3
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 tours/tickets and luggage storage. 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
Harpoon House

Harpoon House

3 out of 5
136 Main St, Southampton, NY
$339 nightly
The price is $387 total per night
$387 total
Oct 5 - Oct 6
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
The Captain Stannard

The Captain Stannard

3 out of 5
138 South Main Street, Westbrook, CT
Free Cancellation
Reserve now, pay when you stay
$238 nightly
The price is $264 total per night
$264 total
Oct 14 - Oct 15
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 a terrace, local meal delivery service, 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
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 24-hour front desk has staff standing by to help with concierge services and securing valuables. Other amenities at this adults-only bed & breakfast include free use of bicycles, a computer station, and free newspapers.
Breakfast included
Pet friendly
Westbrook Inn B&B

Westbrook Inn B&B

3 out of 5
976 Boston Post Rd, Westbrook, CT
$222 nightly
The price is $246 total per night
$246 total
Oct 14 - Oct 15
Total with taxes and fees
Westbrook Inn B&B features free WiFi in public areas, conference space, and coffee in a common area. Free parking is included with your stay. Helpful staff is there to provide luggage storage, as well as offer insight about the area. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a refrigerator in a common area, free use of bicycles, and an arcade/game room.
Breakfast included
Pet friendly
James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
323 Main St, Old Saybrook, CT
$302 nightly
The price is $335 total per night
$335 total
Oct 6 - Oct 7
Total with taxes and fees
Guests staying at James Pharmacy Bed & Breakfast enjoy free WiFi in public areas, express check-out, and a garden. If you drive, take advantage of free parking.
Mill House Inn

Mill House Inn

5 out of 5
31 North Main Street, East Hampton, NY
$303 nightly
The price is $346 total per night
$346 total
Oct 27 - Oct 28
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 concierge services. 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.
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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
    $89 nightly
    The price is $102 total per night from Oct 6 to Oct 7
    $102 total
    Oct 6 - Oct 7
    Total with taxes and fees
    7.8/10 Good! (1,003 reviews)
    Gurney's Montauk Resort & Seawater Spa

    Gurney's Montauk Resort & Seawater Spa

    290 Old Montauk Highway, Montauk, NY
    $372 nightly
    The price is $425 total per night from Oct 30 to Oct 31
    $425 total
    Oct 30 - Oct 31
    Total with taxes and fees
    8.2/10 Very Good! (669 reviews)
    Quality Inn Old Saybrook - Westbrook

    Quality Inn Old Saybrook - Westbrook

    100 Essex Rd, Old Saybrook, CT
    $94 nightly
    The price is $108 total per night from Nov 2 to Nov 3
    $108 total
    Nov 2 - Nov 3
    Total with taxes and fees
    7.6/10 Good! (1,002 reviews)

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
38 B&B
Lowest Price
$102
Highest Price
$447
Popular accommodation
The Sagaponack, The Huntting Inn, Inn at Harbor Hill Marina, Harpoon House, The Captain Stannard, The Hedges Inn, Westbrook Inn B&B, James Pharmacy Bed & Breakfast, Mill House Inn

More to Explore

More to Explore