Photo by Erisa Dilo

Bed and Breakfast in Shelter Island Heights

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 Sept - 14 Sept
In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

Featured B&B in Shelter Island Heights

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (174)
"Great stay!"
The price is NZ$533
includes taxes & fees
6 Oct - 7 Oct
The Sagaponack
The Huntting Inn
Garden

The Huntting Inn

3.5 star property
8.8 out of 10, Excellent, (101)
"Great property."
The price is NZ$948
includes taxes & fees
5 Oct - 6 Oct
The Huntting Inn
Harpoon House
Porch

Harpoon House

3.0 star property
8.4 out of 10, Very good, (136)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
Harpoon House
Inn at Harbor Hill Marina
Property grounds

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1004)
"Homestyle welcome in an incredibly cosy inn!"
The price is NZ$427
includes taxes & fees
1 Oct - 2 Oct
Inn at Harbor Hill Marina
The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (245)
"Everything was fantastic, will stay again!"
The Captain Stannard
The Hedges Inn
Room One: Large Queen Guestroom

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (71)
"Great staff "
The price is NZ$779
includes taxes & fees
9 Sept - 10 Sept
The Hedges Inn
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (162)
"Beautiful place and wonderful staff"
The price is NZ$401
includes taxes & fees
23 Sept - 24 Sept
Westbrook Inn B&B
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
The price is NZ$949
includes taxes & fees
29 Sept - 30 Sept
Mill House Inn
The Homestead
Room, 1 King Bed, Patio, Ground Floor (7)

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (85)
"This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!"
The Homestead
James Pharmacy Bed & Breakfast
Miss Anna James Room

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (18)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
The price is NZ$614
includes taxes & fees
1 Oct - 2 Oct
James Pharmacy Bed & Breakfast
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
9.8 out of 10, Exceptional, (53)
"It’s a very charming place and well located."
Carole's Place B & B
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (64)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
The price is NZ$1,106
includes taxes & fees
1 Oct - 2 Oct
East Hampton Art House Bed & Breakfast
West Neck Guesthouse
Deluxe Room, 1 King Bed

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very good, (37)
"Great property! Close to beach and super clean. "
The price is NZ$608
includes taxes & fees
9 Sept - 10 Sept
West Neck Guesthouse
Vine & Sand
Interior entrance

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (10)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "
Vine & Sand
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (36)
"Great hosts"
434 on Main
Harbor Knoll Bed & Breakfast
Living area

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (10)
"Beautiful bed and breakfast with gorgeous views. Close to shops and restaurants but far enough to be private and quiet. Will definitely be coming back"
Harbor Knoll Bed & Breakfast
Arbor View House B&B
Exterior

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
Arbor View House B&B
Stirling House Bed & Breakfast
Beach/ocean view

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (24)
"Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !"
Stirling House Bed & Breakfast
The 1708 House
Exterior

The 1708 House

3.0 star property
10.0 out of 10, Exceptional, (2)
"We absolutely loved our stay here. The house is stunning, the service is fabulous. The best bed ever to sleep in! Great location and a fabulous breakfast. Thank you. "
The 1708 House
Head of Pond House
Exterior

Head of Pond House

3.0 star property
Head of Pond House
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shelter Island Heights Hotel Reviews

Find out more about Shelter Island Heights

Find out more about Shelter Island Heights

Shelter Island Heights B&B information

Number of reviews
Accommodation
39 B&B
Lowest Price
NZ$401
Highest Price
NZ$1,106

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Searching for B&Bs in Shelter Island Heights?
If you want to find somewhere to stay with a small number of rooms and an intimate environment, a B&B might be a great fit for your trip to Shelter Island Heights. During your time in Shelter Island Heights, you might want to spend some time strolling along the water at Sunset Beach and Crescent Beach.
How do you know if a B&B is a good option for your stay?
With attentive service, opportunities to socialise with other guests and of course a scrumptious breakfast, B&Bs provide a one-of-a-kind setting.
What are the top B&Bs in Shelter Island Heights?
Here are some well-liked B&Bs in the area: West Neck Guesthouse: 6 rooms. 0.6 mi (1 km) from the heart of Shelter Island Heights. The Sagaponack: 10.8 mi (17.4 km) from the city centre. The Captain Stannard: 11 rooms. 14.7 mi (23.6 km) from the city centre. Enjoy the private garden and unique decor. Harpoon House: 9 rooms. Located 13.7 mi (22 km) from the core of Shelter Island Heights. Enjoy the bars and unique decor.
When is the best time to book my B&B in Shelter Island Heights?
When you're dreaming of a trip to Shelter Island Heights, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island Heights is 1452 mm.
What is there to do in Shelter Island Heights?
Travellers looking to spend some time in nature enjoy Shelter Island Heights for its island views and beaches. Spend some time exploring Sunset Beach and Crescent Beach if you're hoping to see some of the area's natural features. You should put Shelter Island Country Club and Sylvester Manor on your list if you want to see more of the area.
How can I get to and around Shelter Island Heights?
You can plan your excursions in and around Shelter Island Heights ahead of time with these transportation options. Fly into East Hampton, NY (HTO), which is located 10.2 mi (16.4 km) away from the heart of the city. Otherwise, you can search for flights to Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.2 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.