Top Winter Vacations - Vacation Rentals in Northwest Woods

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From US $907

         

10.0 (90 Reviews)

House

2026 SUMMER DISCOUNTS! Book Early to receive a 5% discount on monthly rentals!

• Air Conditioner
• Parking
• Pet Friendly

• East Hampton
• Lion Head Beach

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From US $906

         

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New

House

Beautiful East Hampton Retreat with Hot Tub and Pool!

• Parking
• Pet Friendly
• Pool

• East Hampton
• Springs

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From US $664

         

|

7.4 (9 Reviews)

Hotel

EHP Resort & Marina

• Air Conditioner
• Parking
• Pool

• East Hampton
• Springs

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From US $885

         

10.0 (79 Reviews)

House

East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard

• Air Conditioner
• Parking
• Pet Friendly

• East Hampton
• Northwest Harbor

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From US $292

         

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New

House

Bright and Colorful East Hampton Home with Patio!

• Parking
• Pet Friendly
• View

• East Hampton
• Springs

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From US $1,533

         

10.0 (38 Reviews)

House

Quiet Family Friendly Hideaway With Pool And Poolhouse

• Air Conditioner
• Pool
• TV

• New York
• East Hampton

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From US $1,204

         

9.8 (22 Reviews)

House

Beautiful designer modern luxury home - steps from beach

• Air Conditioner
• Parking
• Pet Friendly

• East Hampton
• Northwest Harbor

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From US $4,540

         

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New

Villa

Villa Lylah - Luxury with pool

• Air Conditioner
• Parking
• Pet Friendly

• New York
• East Hampton

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From US $1,000

         

10.0 (19 Reviews)

House

Beautiful Home with walking distance to the beach and new 46ft pool!

• Air Conditioner
• Pet Friendly
• Pool

• East Hampton
• Springs

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From US $555

         

10.0 (27 Reviews)

House

New dates available! Sunny, heated pool, walk to bay beach

• Air Conditioner
• Parking
• Pool

• East Hampton
• Northwest Harbor

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From US $653

         

10.0 (22 Reviews)

House

Ultimate Hamptons Luxury - Modern Home in East Hampton

• Air Conditioner
• Parking
• Pool

• New York
• East Hampton

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From US $1,797

         

10.0 (46 Reviews)

House

Quiet Family Friendly Hideaway With Pool And Poolhouse

• Air Conditioner
• Parking
• Pool

• New York
• East Hampton

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From US $1,553

         

New

House

Gorgeous East Hampton home on Private Harbor

• Air Conditioner
• Parking
• Pet Friendly

• New York
• East Hampton

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From US $1,113

         

9.6 (39 Reviews)

House

STUNNING LUXURY HOME ~ PRIVATE POOL/HOT TUB ~ PERFECT HAMPTONS GETAWAY ~ MBH

• Air Conditioner
• Parking
• Pet Friendly

• East Hampton
• Springs

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From US $760

         

10.0 (95 Reviews)

House

Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings

• Air Conditioner
• Parking
• Pet Friendly

• East Hampton
• Lion Head Beach

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From US $1,583

         

10.0 (60 Reviews)

House

Beautiful East Hampton Home, Pets welcome

• Air Conditioner
• Parking
• Pet Friendly

• East Hampton
• Northwest Harbor

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From US $926

         

10.0 (36 Reviews)

House

New and Ready for Summer 2026! 5-Stars

• Air Conditioner
• Parking
• Pet Friendly

• East Hampton
• Springs

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From US $555

         

10.0 (29 Reviews)

House

Beautiful Home with walking distance to the beach, new 46ft pool! EV charger

• Air Conditioner
• Parking
• Pet Friendly

• East Hampton
• Springs

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From US $1,085

         

10.0 (26 Reviews)

House

MODERN, CHIC, CONTEMPORARY HAMPTON CHATEAU

• Air Conditioner
• Parking
• Pool

• East Hampton
• Northwest Harbor

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From US $1,262

         

10.0 (24 Reviews)

House

Hip & Stylish East Hampton Getaway

• Air Conditioner
• Parking
• Pool

• East Hampton
• Northwest Harbor

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From US $431

         

10.0 (21 Reviews)

Cottage

Cute East Hampton Cottage w/Patio - Walk to Beach

• Air Conditioner
• Parking
• TV

• East Hampton
• Springs

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From US $1,149

         

10.0 (16 Reviews)

House

Perfect Family Retreat-Walk 2 Water, Heated SW Pool, Sauna, Gym- New Kitchen!

• Air Conditioner
• Parking
• Pool

• East Hampton
• Northwest Harbor

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From US $966

         

10.0 (7 Reviews)

House

NEW LISTING- Steps to Private Beach. Completely Remodeled Modern Beach House

• Air Conditioner
• Parking
• Pet Friendly

• East Hampton
• Lion Head Beach

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From US $601

         

10.0 (7 Reviews)

House

East Hampton seaside home

• Air Conditioner
• Parking
• Pet Friendly

• East Hampton
• Springs

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★ Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Northwest Woods.