Brioche buns with chocolate chips priced at $3.50.

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Our top choices for Wainscott Woods hotels

1. Wainscott Woods Retreat

Wainscott Woods Retreat
Wainscott
United States
Ivan
CA $897
CA $1,073 total
includes taxes & fees
Sep 10 - Sep 11
Wainscott Woods Retreat

2. The Sagaponack

The Sagaponack
Wainscott
United States
Jane
CA $351
CA $471 total
includes taxes & fees
Oct 4 - Oct 5
The Sagaponack

3. A Room At The Beach

A Room At The Beach
Bridgehampton
United States
Barbara
CA $457
CA $522 total
includes taxes & fees
Oct 4 - Oct 5
A Room At The Beach

4. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Loretta
CA $383
CA $437 total
includes taxes & fees
Oct 4 - Oct 5
Sag Harbor Inn

5. Bridgehampton Inn

Bridgehampton Inn
Bridgehampton
United States
Leslie
CA $414
CA $473 total
includes taxes & fees
Oct 1 - Oct 2
Bridgehampton Inn

6. East Hampton House Resort

East Hampton House Resort
East Hampton North
Canada
Suzette
CA $343
CA $429 total
includes taxes & fees
Sep 30 - Oct 1
East Hampton House Resort

7. The Maidstone

The Maidstone
East Hampton
United States
Steven
CA $543
CA $652 total
includes taxes & fees
Sep 10 - Sep 11
The Maidstone

8. Zey Hotel

Zey Hotel
Greenport
United States
shaun
CA $234
CA $267 total
includes taxes & fees
Sep 7 - Sep 8
Zey Hotel

9. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Frank
CA $200
CA $263 total
includes taxes & fees
Sep 27 - Sep 28
The Bentley Hotel Southampton

10. Journey East Hampton

Journey East Hampton
East Hampton North
United States
NAKUL
CA $430
CA $540 total
includes taxes & fees
Oct 4 - Oct 5
Journey East Hampton

11. Ocean Vista Resort

Ocean Vista Resort
Amagansett
United States
Michael
CA $176
CA $201 total
includes taxes & fees
Oct 1 - Oct 2
Ocean Vista Resort

12. Hamlet Inn

Hamlet Inn
Southampton
United States
Thomas
CA $175
CA $227 total
includes taxes & fees
Sep 28 - Sep 29
Hamlet Inn

13. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Melissa
CA $280
CA $355 total
includes taxes & fees
Oct 1 - Oct 2
The Shoals Suites and Slips

14. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
United States
Lisa
CA $677
CA $925 total
includes taxes & fees
Sep 24 - Sep 25
The 1770 House Restaurant & Inn

15. Harpoon House

Harpoon House
Southampton
United States
Kim
CA $333
CA $381 total
includes taxes & fees
Sep 7 - Sep 8
Harpoon House

16. The Huntting Inn

The Huntting Inn
Egypt Lane Historic District
United States
James Patrick
CA $616
CA $718 total
includes taxes & fees
Oct 4 - Oct 5
The Huntting Inn

17. Southampton Inn

Southampton Inn
Southampton
United States
Kevin
CA $311
CA $378 total
includes taxes & fees
Oct 4 - Oct 5
Southampton Inn

18. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Joseph
CA $754
CA $947 total
includes taxes & fees
Sep 7 - Sep 8
Faraway Sag Harbor

19. The Hedges Inn

The Hedges Inn
East Hampton
United States
Lauren
CA $746
CA $934 total
includes taxes & fees
Sep 13 - Sep 14
The Hedges Inn

20. The Chequit

The Chequit
The Heights
United States
Kathleen
CA $267
CA $304 total
includes taxes & fees
Oct 4 - Oct 5
The Chequit
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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
Brioche buns with chocolate chips priced at $3.50.
Photo by Miriam Marcus

Top Wainscott Woods Hotel Reviews

 Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Loved our stay! The staff was very helpful. Would definitely stay again!"
Diane 1-night trip
Posted 9 hours ago
Hampton's Vacation Inn
The Hampton Maid

The Hampton Maid

10/10 Excellent
"wonderful hotel."
SABINA 1-night trip
Posted 14 hours ago
The Hampton Maid
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Stutaff was kind and the room was clean. It was very nice to be close to the sea. I had a good time. Thank you"
naoko 1-night trip
Posted 15 hours ago
Ocean Surf Resort
Zey Hotel

Zey Hotel

10/10 Excellent
"Great location, and James is there for your every need! Not posh, but great value and a friendly staff make for a great experience in Greenport!"
Brian 1-night trip
Posted 16 hours ago
Zey Hotel
Kenny's Tipperary Inn

Kenny's Tipperary Inn

8/10 Good
"Nice hotel and very clean, and the staff were very courteous and helpful. Beach is walking distance right down the road. Perfect location if you're looking for something by the beach."
Demetra 4-night trip
Posted 17 hours ago
Kenny's Tipperary Inn
Faraway Sag Harbor

Faraway Sag Harbor

8/10 Good
"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."
Claudia 3-night trip
Posted 18 hours ago
Faraway Sag Harbor
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Great beachfront property! Spa is amazing!"
Daniel 1-night trip
Posted 2 days ago
Gurney's Montauk Resort & Seawater Spa
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"This was a beautiful property on the water. We went to celebrate a birthday and it was the perfect location. The bedrooms were large and had high end toiletries. The restaurants on the property were delicious and had excellent service. It's also pretty centrally located and was only a few minutes from the downtown area. Highly recommend this property."
Arabella 1-night trip
Posted 2 days ago
Montauk Yacht Club
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"A well thought out space. Staff is welcoming and helpful. The Room met our expectations. They even offer a beach pass for the Southampton town beach!"
Victoria 1-night trip
Posted 3 days ago
The Bentley Hotel Southampton

More cheap stays in Wainscott Woods

Kenny's Tipperary Inn

Kenny's Tipperary Inn

432 West Lake Drive Montauk NY
CA $161
CA $191 total
Oct 4 - Oct 5
includes taxes & fees
8.4/10 Very good! (956 reviews)
Kenny's Tipperary Inn
 Hampton's Vacation Inn

Hampton's Vacation Inn

177 West Montauk Highway Hampton Bays NY
CA $171
CA $196 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (394 reviews)
Hampton's Vacation Inn
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
CA $166
CA $224 total
Oct 1 - Oct 2
includes taxes & fees
The Atlantic Hotel
Ocean Surf Resort

Ocean Surf Resort

84 South Emerson Avenue Montauk NY
CA $175
CA $260 total
Sep 27 - Sep 28
includes taxes & fees
8.6/10 Excellent! (303 reviews)
Ocean Surf Resort
Montauk Blue Hotel

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY
CA $205
CA $302 total
Sep 22 - Sep 23
includes taxes & fees
Montauk Blue Hotel
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
CA $361
CA $413 total
Sep 9 - Sep 10
includes taxes & fees
9.2/10 Wonderful! (772 reviews)
The Hampton Maid

Hotels in Wainscott Woods with star rating

Frequently asked questions

What is the best area to stay in Wainscott Woods?
The best area to stay in Wainscott Woods is in the immediate vicinity of the main village centre, particularly along Wainscott Main Street and its adjoining roads.This area is the heart of Wainscott Woods, offering a convenient balance of local amenities and access to the region's natural beauty. It's characterised by its charming, well-maintained homes and a few select local businesses, including a renowned bakery and a couple of independent shops. The layout is relatively spread out, with properties often featuring spacious gardens, providing a sense of privacy and tranquility.Couples looking for a peaceful escape will find this area particularly appealing. The proximity to Wainscott Pond and the nearby ocean beaches means easy access to scenic walks and quiet moments by the water. There are also high-end dining options within a short drive, superb for an evening out.For families, staying near the village centre offers the convenience of being close to essential services while still enjoying a relaxed, residential atmosphere. The open spaces and access to nature provide plenty of opportunities for children to explore.
When is the best time to go to Wainscott Woods?
The best time to visit Wainscott Woods is during the late spring, summer, or early autumn months, from May through to October.The summer, particularly July and August, is when Wainscott Woods truly comes alive. The weather is consistently warm and sunny, great for enjoying the beaches and outdoor activities. This is peak season, so while it's the busiest, it's also when all facilities and attractions are fully operational, offering the widest range of experiences. Expect lovely warm days and pleasant evenings.For those who prefer a slightly quieter experience but still want good weather, June and September are excellent choices. In June, the weather is reliably warm, and the area is less crowded than in the peak summer months. September offers similarly pleasant temperatures, often with the added benefit of slightly cooler evenings and fewer people, making it ideal for relaxing beach days and exploring the local area at a more leisurely pace.Late spring (May) and early autumn (October) also offer a pleasant experience. While the weather can be a little cooler and some establishments might have reduced hours, you'll find great value and a very peaceful environment.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Wainscott Woods.
How much is the nightly rate at a Wainscott Woods hotel?
Prices for hotels in Wainscott Woods often vary, but you can find a great deal from CA $191 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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