Photo by Miriam Marcus

Book Wainscott Woods Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

B&B in Wainscott Woods

The Sagaponack

3.0 star property
Wainscott
8.8 out of 10, Excellent, (210)
"Clean & amenities, staff friendly Thank you "
United States
Archil
$178 nightly
The price is $204
Dec 15 - Dec 16
Total with taxes and fees
The Sagaponack

Mill House Inn

5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (73)
"We stayed at the Inn for our anniversary last weekend. We are devotees of bed and breakfast hotels and loved this one. We arrived to find a huge, and I mean, huge, bouquet of the most beautiful white roses waiting for us in the suite that they upgraded us to. Totally unexpected. These folks could not do enough for us. Breakfast was extremely nice, cooked to order with quality ingredients. Bed was extremely warm and comfortable. The management, the staff, can't say anything negative about...
United States
margaret
$330 nightly
The price is $377
Dec 4 - Dec 5
Total with taxes and fees
Mill House Inn

East Hampton Art House Bed & Breakfast

4.0 star property
Clearwater Beach
9.6 out of 10, Exceptional, (65)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
United States
Dan
$437 nightly
The price is $499
Dec 4 - Dec 5
Total with taxes and fees
East Hampton Art House Bed & Breakfast

Vine & Sand

3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
$320 nightly
The price is $366
Dec 30 - Dec 31
Total with taxes and fees
Vine & Sand

Head of Pond House

3.0 star property
Water Mill
10.0 out of 10, Exceptional, (3)
"Beautiful place with a very kind host. Highly recommend this place!"
United States
Michèle
$527 nightly
The price is $603
Dec 4 - Dec 5
Total with taxes and fees
Head of Pond House

The Huntting Inn

3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (104)
"Staff and management was very welcoming!"
United States
Sanailer
$393 nightly
The price is $447
Dec 16 - Dec 17
Total with taxes and fees
The Huntting Inn

Harpoon House

3.0 star property
Southampton
8.4 out of 10, Very Good, (148)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
United States
Karissa
$286 nightly
The price is $327
Jan 2 - Jan 3, 2026
Total with taxes and fees
Harpoon House

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Southold
10.0 out of 10, Exceptional, (1)
"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...
United States
Jessica P.
$403 nightly
The price is $460
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Large Room w use of pool/tennis in Spacious home

Sag Harbor
$722 nightly
The price is $824
Dec 4 - Dec 5
Total with taxes and fees
Large Room w use of pool/tennis in Spacious home

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Southold
10.0 out of 10, Exceptional, (1)
"Great experience. Wonderful hosts. "
United States
Mark L.
$367 nightly
The price is $420
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Southold
$367 nightly
The price is $420
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Southold
$403 nightly
The price is $460
Jan 1 - Jan 2, 2026
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
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

Top Wainscott Woods Hotel Reviews

Find out more about Wainscott Woods

Wainscott Woods B&B information

Number of reviews
613
Accommodation
33 B&B
Lowest Price
$204
Highest Price
$824

Frequently asked questions

Searching for B&Bs in Wainscott Woods?
If you want to find a place to stay with a small number of rooms and a more personalized environment, a B&B might be just the right fit for your vacation to Wainscott Woods.
How do you know if a B&B is a good option for your stay?
With attentive service, opportunities to interact with the owner, and of course a full breakfast, B&Bs offer a one-of-a-kind environment.
What are the best B&Bs in Wainscott Woods?
Below are some B&Bs in the area: The Sagaponack: 0.6 mi (0.9 km) from the heart of Wainscott Woods.Mill House Inn: 10 rooms. 3.6 mi (5.8 km) from the downtown core. Enjoy the free cooked breakfast and designer toiletries. Harpoon House: 9 rooms. Situated 8.5 mi (13.6 km) from the heart of Wainscott Woods. Enjoy the bars and unique décor. East Hampton Art House Bed & Breakfast: 2 rooms. 8.4 mi (13.5 km) from the heart of downtown. Enjoy the free full breakfast and fitness center. Head of Pond House: 4 rooms. Located 6.4 mi (10.3 km) from the core of Wainscott Woods. Enjoy the outdoor pool and patio area.
When is the best time to stay at a B&B in Wainscott Woods?
When you're dreaming of a escape to Wainscott Woods, be sure to take into account the year-round temperatures. The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Wainscott Woods is 57 inches.
How can I get to and around Wainscott Woods?
Mapping out your trip in and around Wainscott Woods is easy with these transportation options. Fly into East Hampton, NY (HTO), which is located 0.7 mi (1.1 km) from the city center. You can also search for flights into Montauk, NY (MTP), which is 18.9 mi (30.5 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia