Wainscott Woods Holiday Rentals, Wainscott: Private House Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Wainscott Woods

Pet friendly

Apartment

Apart hotel

Pool

Condo

Spa

Family friendly

Hot tub

Waterpark

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Wainscott Woods hotels

Family Studio Suite, 2 Queen Beds | Hypo-allergenic bedding, memory-foam beds, blackout curtains, free WiFi

1. Wainscott Woods Retreat

Wainscott

Ivan

฿26,926

฿31,928 total

includes taxes & fees

23 Sept - 24 Sept

2. The Sagaponack

Wainscott

Jane

฿7,624

฿10,042 total

includes taxes & fees

28 Sept - 29 Sept

3. Topping Rose House

Bridgehampton

Adam

฿32,796

฿37,586 total

includes taxes & fees

21 Sept - 22 Sept

4. Sag Harbor Inn

Sag Harbor

Loretta

฿10,782

฿12,319 total

includes taxes & fees

4 Oct - 5 Oct

The Prestige Coast Suite | Bathroom | Shower, rainfall showerhead, free toiletries, hair dryer

5. A Room At The Beach

Bridgehampton

"I absolutely loved my stay at **A Room at the Beach** in Bridgehampton. Every detail of the property feels thoughtfully designed, creating an atmosphere that is both elegant and incredibly relaxing. The rooms are stylish, comfortable, and well appointed. They strike the perfect balance between luxury and warmth. What really sets this property apart, though, are the charming grounds. They've created gathering spaces that invite you to pause, read, enjoy a morning coffee, and take in the...

Barbara

฿9,854

฿11,258 total

includes taxes & fees

4 Oct - 5 Oct

Graybarn Cottage | Living area | Flat-screen TV, fireplace, DVD player

Graybarn Cottage | Frette Italian sheets, premium bedding, down duvets, pillow-top beds

6. Mill House Inn

Pantigo Road Historic District

Rhett

฿29,119

฿42,085 total

includes taxes & fees

20 Sept - 21 Sept

7. The 1770 House Restaurant & Inn

East Hampton

Lisa

฿15,136

฿20,691 total

includes taxes & fees

19 Oct - 20 Oct

Beach nearby, sun-loungers, beach umbrellas, beach towels

8. The Hedges Inn

East Hampton

Lauren

฿11,950

฿15,617 total

includes taxes & fees

21 Sept - 22 Sept

9. The Huntting Inn

Egypt Lane Historic District

Josie

฿14,819

฿17,264 total

includes taxes & fees

4 Oct - 5 Oct

Seasonal outdoor pool, pool cabanas (surcharge), pool umbrellas

10. Faraway Sag Harbor

Sag Harbor

Miguel

฿14,826

฿18,632 total

includes taxes & fees

4 Oct - 5 Oct

Seasonal outdoor pool, pool umbrellas, pool loungers

Suite, 1 King Bed with Sofa bed | Premium bedding, in-room safe, iron/ironing board (on request)

11. Journey East Hampton

East Hampton North

NAKUL

฿9,205

฿11,568 total

includes taxes & fees

18 Oct - 19 Oct

12. East Hampton House Resort

East Hampton North

Suzette

฿5,248

฿6,902 total

includes taxes & fees

19 Oct - 20 Oct

Beach nearby, white sand, sun-loungers, beach umbrellas

Frette Italian sheets, premium bedding, down duvets, memory-foam beds

13. The Roundtree, Amagansett

Amagansett North

Ryan

฿23,105

฿27,717 total

includes taxes & fees

4 Oct - 5 Oct

Premier Double King Room | Frette Italian sheets, premium bedding, minibar, in-room safe

14. The Maidstone

East Hampton

Steven

฿9,102

฿10,919 total

includes taxes & fees

13 Oct - 14 Oct

Room, 1 King Bed (Pets Allowed) | Premium bedding, soundproofing, iron/ironing board

15. Bridgehampton Inn

Bridgehampton

Leslie

฿9,950

฿11,368 total

includes taxes & fees

1 Oct - 2 Oct

Traditional Cottage, 2 Bedrooms, Lake View (Pet not allowed) | Desk, laptop workspace, iron/ironing board, free WiFi

Traditional Cottage, 2 Bedrooms, Lake View (Pet not allowed) | Living area

16. Head of Pond House

Water Mill

Liz

฿21,565

฿24,638 total

includes taxes & fees

24 Sept - 25 Sept

17. Hamlet Inn

Southampton

Thomas

฿4,218

฿5,452 total

includes taxes & fees

21 Sept - 22 Sept

Cottage | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Premium Cottage | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

18. The Reform Club

Amagansett North

Cathleen

฿32,759

฿40,421 total

includes taxes & fees

6 Oct - 7 Oct

Deluxe King Guest Room | Minibar, in-room safe, desk, laptop workspace

19. Harpoon House

Southampton

Kim

฿8,112

฿9,268 total

includes taxes & fees

1 Oct - 2 Oct

Garden Suite, Wheelchair Accessible, Ground Floor, 2 Queen Beds, Non-Smoking | Premium bedding, minibar, soundproofing, iron/ironing board (on request)

20. Zey Hotel

Greenport

Renee

฿5,623

฿6,424 total

includes taxes & fees

27 Sept - 28 Sept

View all properties

Save an average of 15% on thousands of hotels when you're signed in

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.

Top Wainscott Woods Hotel Reviews

Ocean Resort Inn

8/10 Good

"Small but well maintained room. Great location close to the beach and downtown."

Zey Hotel

10/10 Excellent

"Very pleasant layout, center of town. Common areas are beautiful plus Hakan Bey is very helpful and accommodating"

North Fork Resort

10/10 Excellent

"Very new and clean property very helpful and friendly staff ..... some areas where the rvs are the view not great ..... otherwise all good"

The Atlantic Hotel

10/10 Excellent

"I had room facing the busy street, but the room was well insulated and I did not hear the traffic from outside. Also, the floor plan was very functional. Linen was clean CLEAN, bed was SO comfortable And the amenities of small fridge, coffee maker, iron, -and 2 water bottles provided with each room clean was especially helpful. Parking spaces were wide with ample space to unload and open passenger doors."

Faraway Sag Harbor

10/10 Excellent

"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."

More cheap stays in Wainscott Woods

Kenny's Tipperary Inn

432 West Lake Drive Montauk NY

฿3,852

฿4,577 total

6 Oct - 7 Oct

includes taxes & fees

Hampton's Vacation Inn

177 West Montauk Highway Hampton Bays NY

฿4,118

฿4,705 total

20 Sept - 21 Sept

includes taxes & fees

The Atlantic Hotel

1655 County Road 39 Southampton NY

฿3,973

฿5,373 total

1 Oct - 2 Oct

includes taxes & fees

7.2/10 Good! (1,001 reviews)

Ocean Surf Resort

84 South Emerson Avenue Montauk NY

฿3,627

฿5,592 total

27 Sept - 28 Sept

includes taxes & fees

Montauk Blue Hotel

108 South Emerson Avenue Montauk NY

฿4,050

฿6,256 total

20 Oct - 21 Oct

includes taxes & fees

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY

฿7,047

฿8,051 total

13 Oct - 14 Oct

includes taxes & fees

Frequently asked questions

What's the best place for a stay in Wainscott Woods?

Located 14.3 mi (22.9 km) from the heart of Wainscott Woods, Gurney's Montauk Resort & Seawater Spa is a top choice for your stay, based on our traveller data. Other good choices for your visit to the area are Sound View Greenport and The Atlantic Hotel. See all available top hotels, or 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 as long as you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If your reservation is non-refundable, it might still be possible to cancel it and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Wainscott Woods.

What's the best dog-friendly place to stay in Wainscott Woods?

380 Inn is a top hotel for people travelling 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?

Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and a private beach. Sound View Greenport and The Atlantic Hotel are a couple of other choices that feature an on-site pool. View all hotels with pools in Wainscott Woods.

How is it to stay in Wainscott Woods?

Visitors to Wainscott Woods will definitely find plenty to explore and enjoy. In Wainscott Woods, there are 22 hotels and other accommodation options to choose from. Find out more about Wainscott Woods.

What is there to see 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. Take a look at what more there is 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 temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Wainscott Woods is 1452 mm.

Explore a world of travel with Expedia

More ways to book

Book Hotels in Wainscott Woods on Expedia.com

Find hotels in Wainscott Woods, NY from ฿4,577

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Wainscott Woods

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Wainscott Woods hotels

1. Wainscott Woods Retreat

2. The Sagaponack

3. Topping Rose House

4. Sag Harbor Inn

5. A Room At The Beach

6. Mill House Inn

7. The 1770 House Restaurant & Inn

8. The Hedges Inn

9. The Huntting Inn

10. Faraway Sag Harbor

11. Journey East Hampton

12. East Hampton House Resort

13. The Roundtree, Amagansett

14. The Maidstone

15. Bridgehampton Inn

16. Head of Pond House

17. Hamlet Inn

18. The Reform Club

19. Harpoon House

20. Zey Hotel

Learn more about Wainscott Woods

Top Wainscott Woods Hotel Reviews

Ocean Resort Inn

Zey Hotel

North Fork Resort

The Atlantic Hotel

Faraway Sag Harbor

More cheap stays in Wainscott Woods

Kenny's Tipperary Inn

Hampton's Vacation Inn

The Atlantic Hotel

Ocean Surf Resort

Montauk Blue Hotel

The Hampton Maid

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app