Photo by Miriam Marcus
Search Cottages in Wainscott
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 124 Cottages in Wainscott with updated reviews, rates, and availability.

Orient Village — Historic Bayfront Cottage — 2025 Season
Orient Village — Historic Bayfront Cottage — 2025 Season
10.0 out of 10, Exceptional, (20)

Hampton Cottage.
Hampton Cottage.
10.0 out of 10, Exceptional, (4)

'The Gate House'on Beach front Estate with Dockage. Walk to Village .
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
9.8 out of 10, Exceptional, (91)

Location and views! Located directly on Shinnecock Bay!
Location and views! Located directly on Shinnecock Bay!
9.0 out of 10, Wonderful, (24)

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
10.0 out of 10, Exceptional, (26)

Hamptons Vacation Rental w/ Seasonal Pool!
Hamptons Vacation Rental w/ Seasonal Pool!
10.0 out of 10, Exceptional, (5)

Charming 3-bedroom cottage in fabulous Greenport
Charming 3-bedroom cottage in fabulous Greenport

Southold Cottage w/ Patio & Grill - Walk to Beach!
Southold Cottage w/ Patio & Grill - Walk to Beach!
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
Other property types in Wainscott

Montauk Manor
Montauk Manor
9.2 out of 10, Wonderful, (1182)
The price is AED 617
AED 777 total
includes taxes & fees
27 May - 28 May

Montauk Oceanside Suites
Montauk Oceanside Suites
8.6 out of 10, Excellent, (375)
The price is AED 604
AED 730 total
includes taxes & fees
19 May - 20 May

The Surf Club
The Surf Club
8.6 out of 10, Excellent, (251)
The price is AED 684
AED 981 total
includes taxes & fees
19 May - 20 May
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.
Recent reviews of Wainscott hotels
Recent reviews of Wainscott hotels

The Harbor Front Inn
5/5 Excellent
Gem in Greenport
"My wife and I love this hotel. Perfect situated in the middle of greenport village, walking distance to everything you want/need. They had renovations going on during the day but the hotel remained very clean, room was pristine. We stayed in a harborfront room with balcony, highly recommend, it was so serene! We had a wonderful visit for Mother’s Day. We will definitely be back again. "
A verified traveler stayed at The Harbor Front Inn
Posted 17 hours ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
Top Cottages in Other Destinations
More Accommodation Types in Wainscott
- Vacation Homes in Wainscott
- Apartments in Wainscott
- Villas in Wainscott
- Condo Rentals in Wainscott
- B&B in Wainscott
- Motels in Wainscott
- Guest Houses in Wainscott
- Farmstay in Wainscott
- Aparthotels in Wainscott
- Resorts in Wainscott
- Inns in Wainscott
- Cabin Rentals in Wainscott
- Houseboats in Wainscott
- Condo Resorts in Wainscott
- Hostels in Wainscott
- Residences in Wainscott
- Hotels