Hotels in Wainscott Woods

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Check prices for these dates

This weekend
Jul 10 - Jul 12
Next weekend
Jul 17 - Jul 19

Where to stay in Wainscott Woods?

Exterior

Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (342 reviews)
Stylish rooms in this boutique hotel offer a peaceful retreat after exploring the harbor. Unwind with a drink at the bar, grab a bite at the coffee shop, or bike to nearby Greenport Harbor Brewing Company and Farmers' Market.
The price is $270
$308 total
includes taxes & fees
Jul 27 - Jul 28
Zey Hotel
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
2.0 star property
Hampton Bays
7.4 out of 10, Good, (90 reviews)
Just a 5-minute drive from The Hamptons Beaches, this hotel offers 2 bars/lounges and free WiFi. Only a 3-minute walk from Hampton Bays Station and close to Good Ground Park and Regal UA Hampton Bays for local entertainment.
The price is $167
$191 total
includes taxes & fees
Jul 14 - Jul 15
Hampton Bays Hotel on Main
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (29 reviews)
The price is $372
$425 total
includes taxes & fees
Jul 8 - Jul 9
North Fork Resort
Exterior

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.6 out of 10, Excellent, (773 reviews)
Steps from Riverhead's renowned vineyards, this welcoming motel offers free WiFi and complimentary parking. The 24-hour front desk ensures convenience while clean, comfortable rooms provide a relaxing base to explore nearby Westhampton beaches.
The price is $160
$183 total
includes taxes & fees
Jul 8 - Jul 9
Shorewood Inn
Exterior

Hampton's Vacation Inn

Hampton's Vacation Inn
2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (341 reviews)
This inviting guesthouse offers a refreshing seasonal outdoor pool and tennis courts for active travelers. Located near Hampton Bays Station with easy access to Regal UA Hampton Bays and Good Ground Park, guests enjoy free WiFi and convenient parking.
The price is $225
$257 total
includes taxes & fees
Jul 13 - Jul 14
Hampton's Vacation Inn
Restaurant

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (487 reviews)
This charming Southampton motel offers a refreshing seasonal pool and garden terrace just minutes from Cooper's Beach. Enjoy room conveniences like refrigerators and microwaves after exploring nearby hiking trails or trying kayaking adventures. Free WiFi and parking complete your Hamptons getaway.
The price is $229
$295 total
includes taxes & fees
Jul 19 - Jul 20
Hamlet Inn
Reception

The Penny Lane

The Penny Lane
3.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (84 reviews)
The price is $311
$356 total
includes taxes & fees
Jul 20 - Jul 21
The Penny Lane
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very Good, (42 reviews)
Wake up to a fresh continental breakfast at this coastal B&B offering a seasonal outdoor pool and complimentary bicycles for island exploration. Located near Shelter Island Country Club and Sunset Beach, guests enjoy free WiFi and parking in this tranquil garden setting.
The price is $314
$358 total
includes taxes & fees
Jul 15 - Jul 16
West Neck Guesthouse
Outdoor dining

The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (39 reviews)
Wake to island tranquility at this Shelter Island Heights hotel with premium bedding. Near Shelter Island Country Club and Sunset Beach, this refined retreat offers free WiFi and parking. Convenient to Greenport Station for day trips.
The price is $396
$452 total
includes taxes & fees
Jul 12 - Jul 13
The Chequit
Interior detail

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very Good, (168 reviews)
Escape to Harpoon House, where 3 stylish bars and a charming café await after a day at nearby Hamptons beaches. Free WiFi and parking complement this retreat, with Southampton Station and local museums just a short walk away.
The price is $370
$423 total
includes taxes & fees
Jul 8 - Jul 9
Harpoon House
Property grounds

Barlume Beach Montauk

Barlume Beach Montauk
2.0 star property
Montauk
8.0 out of 10, Very Good, (1 review)
The price is $380
$478 total
includes taxes & fees
Jul 12 - Jul 13
Barlume Beach Montauk
Bar (on property)

The Hampton Maid

The Hampton Maid
2.5 star property
Hampton Bays
9.2 out of 10, Wonderful, (722 reviews)
This tranquil motel offers international cuisine at R.AIRE restaurant and relaxing deep-tissue massages. Just minutes from The Hamptons Beaches with free WiFi and parking. Explore nearby Meschutt Beach or take a quick 3-minute drive to Hampton Bays Station.
The price is $435
$497 total
includes taxes & fees
Jul 8 - Jul 9
The Hampton Maid
Terrace/patio

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (91 reviews)
Perched on the bay, this coastal retreat offers a private beach, outdoor pool, and spa with hydrotherapy treatments. The seasonal restaurant serves local cuisine while proximity to Crescent Beach and Sunset Beach enhances your island getaway.
The price is $592
$744 total
includes taxes & fees
Jul 12 - Jul 13
The Pridwin Hotel
Suite, 1 Queen Bed (The Inn Spot One-Bedroom Suite - Unit) | Living area

The Inn Spot

The Inn Spot
2.0 star property
Hampton Bays
8.0 out of 10, Very Good, (1 review)
The price is $305
$563 total
includes taxes & fees
Jul 30 - Jul 31
The Inn Spot
Exterior

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (291 reviews)
Dive into waterside charm at this Southold retreat on the bay. Located near The Old Field Vineyards and Crescent Beach, the hotel offers free WiFi, bicycles, and a cafe/bar lounge. Travelers consistently praise the helpful staff for enhancing their stay experience.
The price is $413
$497 total
includes taxes & fees
Jul 8 - Jul 9
The Shoals Suites and Slips
View from property

Ocean Vista Resort

Ocean Vista Resort
2.5 star property
Amagansett
9.0 out of 10, Wonderful, (213 reviews)
Wake up to coastal tranquility at this Amagansett retreat with its own private beach access. The indoor pool and relaxing sauna complement your seaside vacation, while in-room refrigerators make beach picnics easy. Enjoy free WiFi and parking near Walking Dunes Trailhead.
The price is $489
$559 total
includes taxes & fees
Jul 8 - Jul 9
Ocean Vista Resort
Reception

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (544 reviews)
Seasonal outdoor pool and complimentary WiFi create a perfect Southampton retreat. Just a 15-minute drive from pristine beaches, with free parking and clean, comfortable rooms. Water adventures await nearby with kayaking options.
The price is $305
$373 total
includes taxes & fees
Jul 14 - Jul 15
The Bentley Hotel Southampton
Exterior

Ocean View Terrace Inn

Ocean View Terrace Inn
2.0 star property
Hampton Bays
8.6 out of 10, Excellent, (125 reviews)
Discover coastal charm at this Hampton Bays motel, just minutes from Cooper's Beach. Unwind with deep-tissue massages after exploring nearby attractions, then cool off in the seasonal outdoor pool. Enjoy complimentary breakfast, WiFi, and parking.
The price is $258
$370 total
includes taxes & fees
Jul 15 - Jul 16
Ocean View Terrace Inn
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (266 reviews)
The price is $374
$470 total
includes taxes & fees
Jul 23 - Jul 24
Cliffside Resort Condominiums
Exterior

Bayview Resort

Bayview Resort
2.5 star property
Hampton Bays
8.8 out of 10, Excellent, (466 reviews)
Soak in seaside tranquility at this Hampton Bays motel featuring a marina and seasonal outdoor pool. Borrow complimentary bicycles to explore nearby attractions like Regal UA Hampton Bays. Enjoy convenient perks including free WiFi, parking, and the fitness center.
The price is $262
$299 total
includes taxes & fees
Jul 12 - Jul 13
Bayview Resort
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

The region around Wainscott Woods is home to attractions such as The Hamptons Beaches and Wolffer Estates Vineyard.

See all hotels in Wainscott Woods
Brioche buns with chocolate chips priced at $3.50.
Photo by Miriam Marcus
Open Photo by Miriam Marcus

Check out reviews of Wainscott Woods hotels guests love

Offshore Montauk

Offshore Montauk

10/10 Excellent
"Everything was fantastic I would go back"
John 3-night trip
Posted 4 hours ago
Offshore Montauk

Frequently asked questions

What hotels do travelers recommend in Wainscott Woods?
Guests like Sag Harbor Inn.
Can I book a refundable accommodation in Wainscott Woods?
If you want the flexibility to change your travel plans to Wainscott Woods, most accommodations offer refundable* rates you can book. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.
Where should I stay in Wainscott Woods if I want a budget-friendly accommodation?
An inexpensive option worth considering is Wainscott Woods Retreat.
Where can I stay in Wainscott Woods if I want a vacation rental instead of a traditional hotel?
If you're looking for a good alternative to a hotel, browse our selection of 18 vacation homes.
What will the weather in Wainscott Woods be like during my vacation?
August and July are typically the warmest months in Wainscott Woods when the average temp is 70°F. January and February are the coldest months when the average temperature is 38°F. October and December are the months with the most rain.
Why should I book my Wainscott Woods hotel with Hotels.com?
There are lots of reasons to book your Wainscott Woods trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.