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Find hotels in Wainscott Woods, NY from ￥17,958

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Dec 26 - Dec 27
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Our top choices for Wainscott Woods hotels

Exterior
Wainscott Woods Retreat

Wainscott Woods Retreat

Wainscott Woods Retreat
2.5 star property
Wainscott
7.0 out of 10, Good, (9)
Situated adjacent to fairways, this serene Wainscott hotel offers complimentary WiFi and parking. Cool off in the seasonal outdoor pool after exploring nearby Wolffer Estates Vineyard. A garden and terrace create perfect spaces for unwinding in Hamptons tranquility.
"Newly Renovated and extremely clean, well kept, and inviting rooms. Staff could not be nicer and more accommodating. Location is ideally situated close to lots of shops, Goldbergs for bagels, East Hampton Beaches etc. Highly recommend this accommodation to anyone staying in the area."
United States
Ivan
The price is ￥55,393
￥63,285 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Wainscott Woods Retreat
Deluxe Double Room, 1 King Bed, City View | In-room safe, individually decorated, individually furnished, desk
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main
2.0 star property
Hampton Bays
7.2 out of 10, Good, (69)
Stylish accommodations near The Hamptons Beaches feature 2 bars/lounges for evening refreshment. Just steps from Hampton Bays Station and minutes from Good Ground Park, this hotel provides free WiFi and cable TV for a comfortable coastal getaway.
"Needed a last minute place to stay and this was PERFECT!! Reasonably priced and the owner is lovely. The rooms have everything you need and there’s a bar on the property where you can play pool and have an after-dinner drink. Highly recommend!"
United States
Olivia
Hampton Bays Hotel on Main
Ocean View 2 Queens | Premium bedding, pillowtop beds, blackout drapes, free WiFi
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (85)
"Hotel was beautiful !!"
United States
Erica
The price is ￥18,105
￥29,593 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Offshore Montauk
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (444)
This charming Southampton motel offers a peaceful garden and terrace. Enjoy easy access to Shinnecock Hills Golf Course while rooms provide convenient refrigerators and microwaves. Hiking trails, kayaking, and free WiFi enhance your stay near scenic beaches.
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ￥13,894
￥17,958 total
includes taxes & fees
Dec 28 - Dec 29
Hamlet Inn
Front of property - evening/night
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1272)
Unwind at this Italian-inspired aparthotel offering both indoor and outdoor swimming. Enjoy Monte's dining, 24-hour fitness center, and in-room kitchenettes. Located minutes from Montauk Station with Shadmoor State Park and Fort Pond nearby.
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is ￥21,613
￥27,744 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Montauk Manor
Seasonal outdoor pool, pool umbrellas, sun loungers
Kenny's Tipperary Inn

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very Good, (879)
Located near Montauk Station, this welcoming motel features a seasonal outdoor pool and garden terrace. Explore neighboring hiking and biking trails or visit Montauk Marine Basin and Gin Beach. Guests praise the helpful staff, clean rooms, free WiFi and parking.
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn
Terrace/patio
Shorewood Inn

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very Good, (711)
Peaceful motel stay with thoughtful staff, clean accommodations, and free WiFi and parking. Explore nearby Sherwood House and Jamesport Vineyards, with convenient access to Mattituck Station just a short drive away.
"Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. "
United States
Mahlon
Shorewood Inn
View from property
House on Chase Creek

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (79)
Escape to this guesthouse on Chase Creek, where a serene golf course setting meets waterfront tranquility. Enjoy convenient self parking and WiFi, plus a welcoming terrace. Shelter Island Country Club and Sylvester Manor await nearby.
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
The price is ￥16,238
￥18,554 total
includes taxes & fees
Jan 6 - Jan 7, 2026
House on Chase Creek
One Bedroom Harbor View Terrace Suite | View from room
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (549)
Set along the waterfront in Greenport, this charming hotel offers a tranquil retreat with easy access to the local train station. Enjoy a refreshing dip in the seasonal outdoor pool or maintain your workout routine at the 24-hour fitness center.
"Awesome stay!!! Great Location "
United States
Bryan
The price is ￥21,075
￥28,319 total
includes taxes & fees
Jan 26 - Jan 27, 2026
The Harbor Front Inn
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (405)
This welcoming hotel offers free WiFi and parking just 15 minutes from The Hamptons Beaches. Enjoy the seasonal outdoor pool after exploring nearby attractions like Sebonack and Shinnecock Hills golf courses, with water activities moments away.
"Room was beautiful and spacious. Staff was courteous and on point. "
United States
Ron
The price is ￥19,512
￥22,449 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Bentley Hotel Southampton
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (600)
Experience coastal luxury at this oceanfront hotel with direct beach access and scenic vistas. Enjoy American fare at The Halyard restaurant or drinks at one of 3 bars including a poolside option. The seasonal outdoor pool, free breakfast, and attentive staff create an idyllic Greenport retreat.
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is ￥20,370
￥27,519 total
includes taxes & fees
Dec 29 - Dec 30
Sound View Greenport
Garden Suite King | Premium bedding, down comforters, individually decorated
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (231)
Discover coastal charm at this waterfront Southold retreat offering free bicycles for exploring nearby wineries. Unwind with drinks at the bar after a day visiting The Old Field Vineyards or relaxing at Crescent Beach, all while enjoying attentive service from the friendly staff.
"Great stay, will definitely go again"
United States
ANTONIO J
The price is ￥25,455
￥29,083 total
includes taxes & fees
Jan 11 - Jan 12, 2026
The Shoals Suites and Slips
Desk, free WiFi, bed sheets
Southampton Long Island Hotel

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (203)
This Southampton hotel offers a convenient home base with free WiFi and parking. Located within a 10-minute drive of Cooper's Beach, guests can enjoy the outdoor pool after exploring nearby attractions and the cultural museum.
"Good location. Nice people!! "
United States
Theresa
The price is ￥17,956
￥21,413 total
includes taxes & fees
Dec 28 - Dec 29
Southampton Long Island Hotel
Exterior
Sea Haven Resort Motel

Sea Haven Resort Motel

Sea Haven Resort Motel
2.0 star property
Southampton
7.8 out of 10, Good, (31)
This welcoming motel offers convenient access to The Hamptons Beaches and Cooper's Beach. Enjoy complimentary WiFi and parking, with Meschutt Beach nearby and 24-hour front desk service. Hampton Bays Station is just a 6-minute drive away.
"Great staff"
United States
Douglas
The price is ￥18,672
￥23,892 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Sea Haven Resort Motel
Exterior
Zey Hotel

Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (290)
Discover charming Greenport from this boutique hotel offering free bicycle rentals for local exploration. Unwind at the bar or grab a bite at the café. The harbor brewery and farmers' market are nearby, with the train station just an 8-minute walk away.
"Loved this place. Lots of places to relax and play games. Super-friendly staff. Can't wait to go back b"
United States
Susie
Zey Hotel
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (975)
Situated by the ocean with outdoor tennis courts and a swimming pool, this Southampton hotel is close to food and shopping. Convenient to Sebonack and Shinnecock Hills Golf Course, with free WiFi and parking. Guests praise the helpful staff.
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel
Outdoor pool, sun loungers
Daunt's Albatross Motel

Daunt's Albatross Motel

Daunt's Albatross Motel
2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (290)
Discover a charming coastal retreat with a seasonal pool and complimentary bicycles to explore Montauk's natural beauty. Just a quick drive from South Edison Beach and Montauk Point, this hotel offers convenient access to hiking trails and water activities.
"Daunts is our home away from home when we visit Montauk. From the convenience to the superb hospitality and comfortable rooms. If you’re visiting MTK you have to stay at Daunts, and their pet friendly "
United States
Yohayna
Daunt's Albatross Motel
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (142)
Soak in bay vistas at this Greenport beach hotel with 2 bars and 3 dining options. After a massage at the full-service spa, grab a complimentary bike to explore nearby Railroad Museum and East End Seaport Maritime Museum.
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows
View from room
Hero Beach Club

Hero Beach Club

Hero Beach Club
4.0 star property
Montauk
9.0 out of 10, Wonderful, (202)
This Montauk motel offers beachside relaxation with spa services and a welcoming bar/lounge. Surrounded by gardens and featuring a lovely terrace, it provides free WiFi and parking near Second House Museum and Kirk Park Beach.
"Great weekend trip "
United States
Timothy
The price is ￥36,603
￥57,676 total
includes taxes & fees
Dec 27 - Dec 28
Hero Beach Club
Exterior
The Sagaponack

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (215)
Escape to this Wainscott retreat featuring free WiFi and parking. Located only 5 minutes from pristine Hamptons shorelines and Wolffer Estates Vineyard. The attentive staff receives consistent praise while the refreshing outdoor pool enhances summer stays.
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is ￥24,117
￥33,789 total
includes taxes & fees
Jan 8 - Jan 9, 2026
The Sagaponack
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.
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Learn more about Wainscott Woods

Check out Wolffer Estates Vineyard and Georgica Beach—just a couple of the sights around Wainscott Woods.

See all hotels in Wainscott Woods
If I could only "Trove" a smell. Delicious scones and brioches (cinnamon butter and chocolate chip options), etc.
Photo by Miriam Marcus
Open Photo by Miriam Marcus

Top Wainscott Woods Hotel Reviews

Montauk Manor

Montauk Manor

10/10 Excellent
"Beautiful place as always, love the hot tub and sauna."
Joseph 2-night trip
Posted 4 days ago
Montauk Manor

More cheap stays in Wainscott Woods

Hamlet Inn

Hamlet Inn

300 Montauk Highway Southampton NY
The price is ￥13,894 per night from Dec 28 to Dec 29
￥13,894
￥17,958 total
Dec 28 - Dec 29
includes taxes & fees
8.4/10 Very Good! (444 reviews)

Frequently asked questions

What's the best place for a stay in Wainscott Woods?
Wainscott Woods Retreat is one of the top choices for your stay based on our traveler data. This hotel offers free parking and private balconies. Other good choices for your stay in the area are Gurney's Montauk Resort & Seawater Spa and Sound View Greenport. See all available top hotels, or vacation rentals in Wainscott Woods.
What's the top vacation rental that Wainscott Woods has to offer?
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available: You might want to consider this vacation home rental near Wainscott Woods, which is located near the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation. See all vacation rentals in Wainscott Woods.
If I need to cancel my hotel reservation in Wainscott Woods, will I receive a refund?
Yes! The majority of room reservations are fully refundable if cancelled prior to the hotel's cancellation deadline, which often is within 24-48 hours of the scheduled arrival. If you have a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Wainscott Woods.
Where can I learn more about changing or cancelling my trip to Wainscott Woods?
For additional details about picking new dates or cancelling your trip to Wainscott Woods, go to https://www.expedia.com/service/.
What's the best pet-friendly place to stay in Wainscott Woods?
380 Inn is a top hotel for people traveling with their pets, and offers free newspapers and in-room kitchenettes for its human guests. See more pet-friendly hotel accommodations in Wainscott Woods.
What are some hotels with pools in Wainscott Woods?
Wainscott Woods Retreat: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Gurney's Montauk Resort & Seawater Spa and Sound View Greenport are a couple of other choices that feature an onsite pool. View all hotels with pools in Wainscott Woods.
What's it like staying in Wainscott Woods?
Visitors to Wainscott Woods are sure to find plenty to explore and enjoy. In Wainscott Woods, there are 22 hotels and other accommodations to choose from. Find out more about Wainscott Woods.
What should I see while I'm in Wainscott Woods?
Places to visit in the wider area include Wolffer Estates Vineyard, Georgica Beach, and The Jewish Center of the Hamptons. You'll also find East Hampton Main Beach and Guild Hall in the area. Check out what more to see and do in Expedia's Wainscott Woods guide.
What's the weather like in Wainscott Woods?
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.

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