Wainscott Woods Holiday Rentals, Wainscott: Private House Rentals

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Go beyond your typical stay in Wainscott Woods

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Spa

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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

Rp11.498.112

Rp13.757.633 total

includes taxes & fees

10 Sept - 11 Sept

2. The Sagaponack

Wainscott

Jane

Rp4.508.605

Rp6.039.230 total

includes taxes & fees

4 Oct - 5 Oct

Carriage House | Living area | Flat-screen TV

3. The 1770 House Restaurant & Inn

East Hampton

Lisa

Rp8.672.380

Rp11.855.654 total

includes taxes & fees

21 Sept - 22 Sept

4. Sag Harbor Inn

Sag Harbor

Loretta

Rp5.755.212

Rp6.575.330 total

includes taxes & fees

4 Oct - 5 Oct

5. Topping Rose House

Bridgehampton

Adam

Rp17.486.712

Rp20.040.673 total

includes taxes & fees

10 Sept - 11 Sept

6. Bridgehampton Inn

Bridgehampton

Leslie

Rp5.311.137

Rp6.068.018 total

includes taxes & fees

1 Oct - 2 Oct

7. East Hampton House Resort

East Hampton North

Suzette

Rp4.396.343

Rp5.505.819 total

includes taxes & fees

28 Sept - 29 Sept

8. The Huntting Inn

Egypt Lane Historic District

James Patrick

Rp7.910.042

Rp9.214.734 total

includes taxes & fees

4 Oct - 5 Oct

Standard Room, 1 King Bed | Premium bedding, down duvets, minibar, in-room safe

40-inch flat-screen TV with digital channels, TV, Netflix

9. The Hampton Maid

Hampton Bays

SABINA

Rp4.631.184

Rp5.291.129 total

includes taxes & fees

8 Sept - 9 Sept

Seasonal outdoor pool, pool umbrellas, pool loungers

10. Journey East Hampton

East Hampton North

NAKUL

Rp5.510.971

Rp6.925.794 total

includes taxes & fees

4 Oct - 5 Oct

1 bedroom, premium bedding, down duvets, in-room safe

55-inch Smart TV with cable channels, TV

11. The Bentley Hotel Southampton

Southampton

Frank

Rp2.565.014

Rp3.374.604 total

includes taxes & fees

27 Sept - 28 Sept

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

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

12. The Roundtree, Amagansett

Amagansett North

Ryan

Rp12.332.446

Rp14.794.299 total

includes taxes & fees

1 Oct - 2 Oct

13. Southampton Long Island Hotel

Southampton

William

Rp3.531.056

Rp4.211.006 total

includes taxes & fees

16 Sept - 17 Sept

14. Southampton Inn

Southampton

Kevin

Rp3.996.675

Rp4.855.516 total

includes taxes & fees

4 Oct - 5 Oct

Suite, 1 Bedroom, Terrace, Harbour View | Terrace/patio

Suite, 1 Bedroom, Terrace, Harbour View | Frette Italian sheets, premium bedding, down duvets, pillow-top beds

Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers

15. The Harbor Front Inn

Greenport

Michael

Rp4.620.156

Rp5.785.839 total

includes taxes & fees

4 Oct - 5 Oct

Deluxe Double Room, 1 King Bed, City View | In-room safe, desk, laptop workspace, free WiFi

Comfort Double Room | Private kitchenette | Coffee/tea maker, mini-fridge

16. Hampton Bays Hotel on Main

Hampton Bays

Deborah

Rp2.095.857

Rp2.394.517 total

includes taxes & fees

8 Sept - 9 Sept

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

Luxury Suite, Lake View (Pet not allowed) | Desk, laptop workspace, iron/ironing board, free WiFi

17. Head of Pond House

Water Mill

Liz

Rp33.216.768

Rp37.950.158 total

includes taxes & fees

9 Sept - 10 Sept

18. Hamlet Inn

Southampton

Thomas

Rp2.251.460

Rp2.910.112 total

includes taxes & fees

27 Sept - 28 Sept

Bay Twin Room | Minibar, in-room safe, individually decorated, individually furnished

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

19. 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

Rp5.844.027

Rp6.676.756 total

includes taxes & fees

4 Oct - 5 Oct

Honeymoon Room, Jetted Tub | Egyptian cotton sheets, premium bedding, desk, laptop workspace

Single Room | Egyptian cotton sheets, premium bedding, desk, laptop workspace

20. The Atlantic Hotel

Southampton

Jessa

Rp2.118.237

Rp2.864.162 total

includes taxes & fees

1 Oct - 2 Oct

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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.

Top Wainscott Woods Hotel Reviews

Hampton's Vacation Inn

10/10 Excellent

"Loved our stay! The staff was very helpful. Would definitely stay again!"

The Hampton Maid

10/10 Excellent

"wonderful hotel."

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"

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!"

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."

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."

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent

"Great beachfront property! Spa is amazing!"

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."

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!"

More cheap stays in Wainscott Woods