Skip to main content

The 7 Best B&Bs in Southold, USA

Check out our pick of great B&Bs in Southold

Filter by:


Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

See the latest prices and deals by choosing your dates.

Relax on the large wrap-around front porch of this Long Island, New York bed and breakfast. Free Wi-Fi and daily breakfast are offered. Cedar Beach is 1 mile away.

Each uniquely styled room at A Walk in the Woods Bed and Breakfast features en suite bathroom. Decorated with antique accents, these rooms include a seating area.

Owner Flo was lovely, extremely helpful and attentive. She made us very welcome in her beautiful home.

Show more Show less
9.2
Superb
41 reviews
Price from
£313
per night

Offering free bike hire and free WiFi access, Historic White Blosson House is a uniquely furnished inn located in Southold. The property features scenic gardens.

Patio access is included with the self-catering apartment. The kitchenette is equipped with an oven and a dishwasher. The bathroom has free toiletries.

The apartment was so quaint, well kept property. Quiet area, very close to local beaches ...great stay!!!

Show more Show less
8.7
Fabulous
14 reviews
Price from
£252
per night

Cable TVs are provided in each room at Seven - a boutique B&B on Shelter Island. Featuring a seating area, rooms also include a private bathroom with a hairdryer and free toiletries including sustainable amenities from Cold Spring Apothecary Natural French milled soaps from Pre de Provence.

This was exactly what I was looking for - the owner was very, very sweet and the place was ideal. We loved the swimming pool and all the other amenities and I will definitely come again.

Show more Show less
9.9
Exceptional
25 reviews
Price from
£309
per night

At the bed and breakfast, every unit comes with a wardrobe. With a private bathroom fitted with a bath and bathrobes, units at the bed and breakfast also boast free WiFi, while certain rooms are fitted with a balcony. All units will provide guests with air conditioning, a safety deposit box and a flat-screen TV.

Very easy contactless check in, Suzanne was great with communication and accommodating requests and making sure we had a great short trip!

Show more Show less
9.1
Superb
11 reviews
Price from
£170
per night

Offering a sun terrace and views of the sea, The Chequit is located in Shelter Island Heights, 44 km from Mystic. Guests can enjoy the on-site restaurant. Free WiFi is available throughout the property and free private parking is available on site.

Every room at this inn is air conditioned. Rooms include a private bathroom. Extras include free toiletries and a hair dryer.

Show more Show less
9
Superb
1 reviews
Price from
£441
per night

All units feature air conditioning and a cable flat-screen TV. There is a private bathroom with shower in some units, along with bathrobes, slippers and a hair dryer. At the bed and breakfast, every unit includes bed linen and towels.

A perfect location, with warm and friendly hospitality. Such a pleasure to be in an idyllic setting.

Show more Show less
8.8
Fabulous
31 reviews
Price from
£293
per night

At the bed and breakfast, all units are fitted with a wardrobe. Featuring a private bathroom with a shower and bathrobes, units at the bed and breakfast also have free WiFi, while some rooms also offer a terrace. At the bed and breakfast, the units have air conditioning and a flat-screen TV.

Relaxing atmosphere, very interesting place, beautifully decorated.

Show more Show less
8.7
Fabulous
134 reviews
Price from
£273
per night

This Greenport bed and breakfast is located on the water and offers free Wi-Fi and individually decorated rooms equipped with electric fireplaces. Island’s End Golf & Country Club is 2 miles away.

The Greenport Stirling House B&B is a half mile from the beach area. A ferry service is also available to Shelter Island.

The owner's homemade bread and baking stuff were very delicious! The best breakfast I ever had in B&B in the States. Location is also good, walking distance from the Town center but very quiet location in front of the sea.

Show more Show less
9.6
Exceptional
34 reviews
Price from
£299
per night

Situated within 2.7 km of Fleet Neck Beach and 25 km of Splish Splash, Sweet Dreams Bed and Breakfast Cutchogue features rooms with air conditioning and a shared bathroom in Cutchogue. This property offers access to a patio and free private parking. Boasting family rooms, this property also provides guests with a picnic area.

clean, great proprietor, nice inside and outside space

Show more Show less
9.7
Exceptional
12 reviews
Price from
£405
per night

This historic bed and breakfast in Long Island features free Wi-Fi, spa services, and individually decorated rooms equipped with a flat-screen TV. Island End Golf and Country Club is less than a mile away.

The B&B is surrounded by a beautiful large garden and is run by a really nice couple, Veda and Wilfred. The rooms are each unique and tastefully furnished. The morning coffee is served up to the room, which we really appreciated. Breakfast was just amazing! Veda always prepared an excellent 3-course breakfast. We really enjoyed the company of the hosts and other guests and missed these morning talks the rest of our trip. It was really fun! Thank you, Veda and Wilfred, for 5 unforgettable days that made our trip to LI so special!

Show more Show less
9.6
Exceptional
10 reviews
Price from
£335
per night

Looking for a B&B?

For travellers who enjoy beauty in the simple things, a bed and breakfast (B&B) is the perfect place for a getaway. Hosts welcome guests into their homes and provide a private room and complimentary breakfast. Bathrooms may be shared by other guests, and there is often shared space with the host.
Search B&Bs in Southold

Research, refine and make plans for your whole trip