Photo by Miriam Marcus

Search Cottages in Wainscott

    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
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

Compare 129 Cottages in Wainscott with updated reviews, rates, and availability.

Fairy Tale Guest Cottage in Magic Garden by Pool
Outdoor pool

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (66)
"Enjoyed our stay very much. Place is beautiful, clean, hosts cannot b nicer. Definitely hope to return "
Fairy Tale Guest Cottage in Magic Garden by Pool
Location and views! Located directly on Shinnecock Bay!
Smart TV

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (24)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
Location and views! Located directly on Shinnecock Bay!
Cozy cottage on Fort Pond Lake.
Miscellaneous

Cozy cottage on Fort Pond Lake.

10.0 out of 10, Exceptional, (12)
"Great location! We loved our stay at the cottage and can’t wait to return. Danny was so easy to communicate with and he really went the extra mile to make sure we enjoyed our stay. "
Cozy cottage on Fort Pond Lake.
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Beach nearby, sun loungers, beach towels

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

10.0 out of 10, Exceptional, (26)
"The property was clean, exactly as advertised and extremely cozy and convenient. The host was super helpful and quick to respond!"
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Orient Village — Historic Bayfront Cottage — 2025 Season
Exterior

Orient Village — Historic Bayfront Cottage — 2025 Season

10.0 out of 10, Exceptional, (20)
"We had an amazing time enjoying the house and exploring the area. Fishing wasn’t fantastic, but that’s nobody’s fault. Would definitely go back!"
Orient Village — Historic Bayfront Cottage — 2025 Season
Fabulous Waterfront Property in the Heart of Wine Country
Sun loungers, beach towels

Fabulous Waterfront Property in the Heart of Wine Country

10.0 out of 10, Exceptional, (174)
"Beautiful and cozy lakeside retreat. Super serene and peaceful place to stay."
Fabulous Waterfront Property in the Heart of Wine Country
Sabbatical a Private guest cottage in Sag Harbor
Exterior

Sabbatical a Private guest cottage in Sag Harbor

9.6 out of 10, Exceptional, (9)
"I can’t thank enough our hostess Susan for her amazing hospitality and kindness! I strongly recommend her place to stay for vacation!"
Sabbatical a Private guest cottage in Sag Harbor
Ritz - East Hampton Cottage On The Water
Smart TV

Ritz - East Hampton Cottage On The Water

10.0 out of 10, Exceptional, (6)
"We enjoyed our time in the Ritz. It’s a great cottage surrounded by waterfront activities. The host was accommodating and welcoming."
Ritz - East Hampton Cottage On The Water
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Miscellaneous

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (91)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
The price is SAR 1,032
SAR 1,307 total
includes taxes & fees
8 Jun - 9 Jun
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays
Miscellaneous

Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays

2.0 star property
10.0 out of 10, Exceptional, (2)
"Excellent Host, great stay, beautiful property and set up and very modern."
Charming Modern Cottage by the Bay and Beach - 3 bedroom/2 baths - Hampton Bays
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
TV, fireplace, video games, DVD player

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.6 out of 10, Excellent, (25)
"The cottage was perfect for my small family and our dog. It was super clean, great location and adorable vibe. We will definitely be back! "
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday
Smart TV, fireplace, music library, stereo

Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday

9.6 out of 10, Exceptional, (44)
"A lovely beach cottage with bay views and easy walking access to the Atlantic beaches.The place was cozy and clean with expansive open views across reserve land to the bay.A bit tricky to find off the highway at night but we eventually got our bearings!"
Bright White Beach House, Just a Short Stroll to Ocean- A Sunset to End Everyday
Walk to Love Lane! Immaculately renovated private cottage.
Dining

Walk to Love Lane! Immaculately renovated private cottage.

10.0 out of 10, Exceptional, (16)
"My wife and I stayed for the weekend for our Anniversary and this was the perfect location. Quaint and quite hideout with tons to do nearby."
Walk to Love Lane! Immaculately renovated private cottage.
Hidden gem! Southampton beach cottage
Fridge, microwave, oven, stovetop

Hidden gem! Southampton beach cottage

The price is SAR 746
SAR 2,198 total
includes taxes & fees
15 Jun - 16 Jun
Hidden gem! Southampton beach cottage
Charming and Bright Cottage with Salt Water Pool
Smart TV

Charming and Bright Cottage with Salt Water Pool

10.0 out of 10, Exceptional, (5)
"What a beautiful cottage. Clean and bright. Would definitely stay again!"
Charming and Bright Cottage with Salt Water Pool
Luxurious 3 BR Cottage w/ Ocean View Balcony
A heated pool

Luxurious 3 BR Cottage w/ Ocean View Balcony

Luxurious 3 BR Cottage w/ Ocean View Balcony
East Hampton/Springs Cottage- minutes walk to sea
Beach nearby

East Hampton/Springs Cottage- minutes walk to sea

10.0 out of 10, Exceptional, (4)
"We really enjoyed this quaint cottage that really felt lovely me home. Very clean and well equipped Had a great time"
East Hampton/Springs Cottage- minutes walk to sea
Hampton Cottage.
Smart TV

Hampton Cottage.

10.0 out of 10, Exceptional, (4)
"charming small cottage, very fresh, crisp, and comfortable! 100% redone, everything is brand new! we might have been the first guest. good location for Hamptons travel & shopping & beaches fun restaurants & music nearby, Cowfish, Roomba, Canal Cafe, Francesco Pizza-Gelato. Mrs and I had a wonderful time, cheers!"
Hampton Cottage.
Lovely Cottage in the Heart of Long Island Wine country
Beach

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (25)
"we had such a fun weekend out in southold! Cottage was perfect for us for a cold rainy weekend. Everything was so close to the house. Will definitely be back in the summer!"
Lovely Cottage in the Heart of Long Island Wine country
Walk to Breakwater Beach in Heart of Wine Country
Beach nearby

Walk to Breakwater Beach in Heart of Wine Country

9.8 out of 10, Exceptional, (12)
"My wife and I traveled with our son and dog to Mattituck and had a great stay at this home. It was very comfortable and clean, and the host was easy to communicate with. I highly recommend staying here."
Walk to Breakwater Beach in Heart of Wine Country
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

Frequently asked questions

Why book your cottage in Wainscott with Expedia?
Booking a cottage in Wainscott is as easy as working out your travel dates and choosing your ideal place for a vacation in the outdoors. From chic retreats to budget-friendly stays and cottages that have amenities like a kitchenette, Expedia has something for all tastes. As for awesome deals? We’ve have them as well!
How can I find cheap cottages in Wainscott?
The simplest way to track down cheap cottages in Wainscott is with Expedia’s user-friendly filter tool. Narrow your search results by amenities, budget and star rating to snag unbeatable deals in just a few keystrokes.