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Oct 15 - Oct 16
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Oct 16 - Oct 17
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Oct 16 - Oct 18
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Our top choices for Wainscott Woods hotels

1. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Terri
CA $311
CA $356 total
includes taxes & fees
Nov 2 - Nov 3
Sag Harbor Inn

2. East Hampton House Resort

East Hampton House Resort
East Hampton North
United States
Tina
CA $226
CA $296 total
includes taxes & fees
Nov 2 - Nov 3
East Hampton House Resort

3. The Sagaponack

The Sagaponack
Wainscott
United States
Jane
CA $286
CA $383 total
includes taxes & fees
Nov 15 - Nov 16
The Sagaponack

4. Journey East Hampton

Journey East Hampton
East Hampton North
United States
Erika
CA $352
CA $442 total
includes taxes & fees
Nov 4 - Nov 5
Journey East Hampton

5. The Maidstone

The Maidstone
East Hampton
United States
Steven
CA $312
CA $375 total
includes taxes & fees
Nov 1 - Nov 2
The Maidstone

6. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
United States
Doug
CA $203
CA $232 total
includes taxes & fees
Oct 28 - Oct 29
The Bentley Hotel Southampton

7. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Thomas
CA $538
CA $676 total
includes taxes & fees
Nov 8 - Nov 9
Faraway Sag Harbor

8. A Room At The Beach

A Room At The Beach
Bridgehampton
United States
Samantha
CA $421
CA $481 total
includes taxes & fees
Nov 2 - Nov 3
A Room At The Beach

9. Bridgehampton Inn

Bridgehampton Inn
Bridgehampton
United States
Leslie
CA $425
CA $486 total
includes taxes & fees
Nov 2 - Nov 3
Bridgehampton Inn

10. The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
East Hampton
United States
Lisa
CA $572
CA $782 total
includes taxes & fees
Nov 2 - Nov 3
The 1770 House Restaurant & Inn

11. The Huntting Inn

The Huntting Inn
Egypt Lane Historic District
Canada
Josie
CA $545
CA $636 total
includes taxes & fees
Nov 2 - Nov 3
The Huntting Inn

12. Mill House Inn

Mill House Inn
Pantigo Road Historic District
United States
Rhett
CA $462
CA $668 total
includes taxes & fees
Nov 2 - Nov 3
Mill House Inn

13. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
CA $828
CA $950 total
includes taxes & fees
Oct 18 - Oct 19
Topping Rose House

14. Ocean Vista Resort

Ocean Vista Resort
Amagansett
United States
Dan
CA $206
CA $235 total
includes taxes & fees
Oct 18 - Oct 19
Ocean Vista Resort

15. The Hedges Inn

The Hedges Inn
East Hampton
United States
Lauren
CA $511
CA $668 total
includes taxes & fees
Oct 18 - Oct 19
The Hedges Inn

16. The Atlantic Hotel

The Atlantic Hotel
Southampton
United States
Chris
CA $149
CA $206 total
includes taxes & fees
Oct 29 - Oct 30
The Atlantic Hotel

17. Hamlet Inn

Hamlet Inn
Southampton
United States
Eric
CA $226
CA $293 total
includes taxes & fees
Nov 13 - Nov 14
Hamlet Inn

18. Southampton Inn

Southampton Inn
Southampton
United States
Kevin
CA $284
CA $348 total
includes taxes & fees
Nov 6 - Nov 7
Southampton Inn

19. The Chequit

The Chequit
The Heights
United States
Patrick
CA $211
CA $241 total
includes taxes & fees
Nov 8 - Nov 9
The Chequit

20. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Masayo
CA $264
CA $337 total
includes taxes & fees
Nov 8 - Nov 9
The Shoals Suites and Slips
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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

Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"Lovely stay! Great ocean views from the room and balcony. Staff were very helpful and friendly."
Joan 1-night trip
Posted 2 hours ago
Montauk Blue Hotel
Zey Hotel

Zey Hotel

10/10 Excellent
"The staff particularly James were over the top accommodating!!"
William 2-night trip
Posted 20 hours ago
Zey Hotel
Shorewood Inn

Shorewood Inn

10/10 Excellent
"Clean, affordable, helpful staff, good parking. We will stay again when we are in the area."
Kathleen 1-night trip
Posted 22 hours ago
Shorewood Inn
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

10/10 Excellent
"Everything was wonderful…location, view, amenities made our stay so memorable. Can’t wait to go back!"
SUZANNE 3-night trip
Posted 1 day ago
Beachcomber Resort at Montauk
Offshore Montauk

Offshore Montauk

10/10 Excellent
"This was my first time staying @ this property. The staff were so kind & helpful! The gentleman at the front desk was beyond helpful from the moment we checked in, to the moment we left! This team knows the meaning of hospitality! 5 star service Would stay here again !! Thank you :)"
guadalupe 1-night trip
Posted 2 days ago
Offshore Montauk
Sound View Greenport

Sound View Greenport

10/10 Excellent
"The breakfast could have had a better choice."
Allen 1-night trip
Posted 2 days ago
Sound View Greenport
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Booked a 1bedroom king suite and it was fabulous! Tons of room; full size refrigerator; comfy mattress and suite was so clean. Second time here and returning in 2 months. Staff very pleasant and accommodating, especially the manager, Leah."
Cynthia 7-night trip
Posted 2 days ago
The Bentley Hotel Southampton
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Perfect for weekend stay"
DAWN 1-night trip
Posted 11 days ago
Ocean Surf Resort
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

10/10 Excellent
"This hotel was clean, comfy and reasonably priced. Everything worked out well virtually checking in and was perfect for our one night stay. Parking was a little nerve racking since there was no parking on the premise but the street parking worked out well reading the street signs and moving the car when necessary."
Richard 1-night trip
Posted 12 days ago
Hampton Bays Hotel on Main

More cheap stays in Wainscott Woods

Kenny's Tipperary Inn

Kenny's Tipperary Inn

432 West Lake Drive Montauk NY
CA $153
CA $182 total
Nov 5 - Nov 6
includes taxes & fees
Kenny's Tipperary Inn
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
CA $149
CA $206 total
Oct 29 - Oct 30
includes taxes & fees
The Atlantic Hotel
Ocean Surf Resort

Ocean Surf Resort

84 South Emerson Avenue Montauk NY
CA $133
CA $214 total
Oct 29 - Oct 30
includes taxes & fees
8.6/10 Excellent! (329 reviews)
Ocean Surf Resort
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
CA $203
CA $232 total
Oct 28 - Oct 29
includes taxes & fees
9.6/10 Exceptional! (600 reviews)
The Bentley Hotel Southampton
Sun N Sound

Sun N Sound

22 Soundview Drive Montauk NY
CA $197
CA $249 total
Oct 19 - Oct 20
includes taxes & fees
9.2/10 Wonderful! (334 reviews)
Sun N Sound
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
CA $301
CA $344 total
Oct 19 - Oct 20
includes taxes & fees
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 $182 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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