Vacation rentals in Wainscott

Near apple/pumpkin picking ~ 8 mins to Main Street

The perfect Hamptons getaway! Near all of the best attractions. Enjoy this chic, serene home surrounded by the beauty of Hamptons nature + birds' chirping, deer sauntering. Cozy up to the wood burning fireplace, 80' TV + Chef's kitchen. Spark up the BBQ + firepit under the starry sky! Enjoy the bucolic views from every room. Here, you will be 8 minutes to Main St of East Hampton + Amagansett for endless dining + shopping options! Also 5-10 minutes to gorgeous beaches (great any time of year!).

Family · Location · Quiet

Stylish Artist's Home in EH 4B, Pool, Paradise

Enjoy time in a stylish and comfortable artist's home in East Hampton. Quick access to beaches and activities in East Hampton, Sag Harbor, Bridgehampton and Wainscott. Also enjoy trendy dining in East Hampton/Sag Harbor. Outdoor fun can be had at the pool, around the fire pit and with the grill. This house can sleep up to 8 people and brings stylish comfort to your Hamptons experience. The home has all amenities. Open to longer rentals - discounts are available for weekly and monthly rentals.

Location · Value · Comfort

Beautiful E. Hampton Home w/ Brand New heated pool

RECENTLY RENOVATED BASEMENT LEVEL SEE PICS Charming and beautifully designed, our East Hampton home is the perfect getaway. Enjoy a HEATED pool and easy access to local attractions - we're just 2 miles from the village and a short drive to the beach. Inside, you'll find three large HD TVs with cable and internet, as well as gas grill for summer fun. Our private entry lower apartment includes a kitchenette, full bath, and many extras. Book your stay today and experience luxury and relaxation!

Value · Location · Backyard

Hamptons Waterfront Getaway – Stylish & Serene

Waterfront Luxury Retreat in Sag Harbor. As featured in Vogue, Mansion Global, and Homeworthy. This serene designer home offers direct bay access for kayaking and paddle boarding, plus a private path to Clam Island for peaceful walks and beach picnics. Enjoy a gourmet kitchen with Viking and Sub-Zero appliances, spa-like en-suite baths, and plush bedding. Minutes to bay beaches and Sag Harbor village—your private escape awaits. Ideal for romantic getaways, relaxing weeks, or a summer reset.

Family · Location · Quiet

Serene East Hampton Escape - Warm Pool til Nov

A luxuriously curated woodland escape with massive pool (heated and open May through October), fully fenced and just minutes from EH Village & Ocean Beaches. This impeccably renovated four-bedroom, four-and-a-half-bath home offers refined comfort in a serene, private setting. Sunlight floods the expansive interiors, featuring rich luxurious finishes, a separate office with queen sofa bed, a freestanding soaking tub, and a designer chef’s kitchen with a custom dining table for ten or more.

Location · Family · Accuracy

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Relax with friends / family at this home in a magical setting overlooking Lily pond Completely private but 5 mins to Sag Harbor downtown, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds, 2.5 baths - 50ft heated Gunite pool (125/d extra to heat) - Outdoor deck overlooking pond -Amazing views! - Fire pit with Adirondack chairs Unique house to unwind while being close to the action. NOTE: Due to water leakage issues, the bath in pool house is not available

Value · Location · Decor

Quintessential Hamptons Home

Large Hamptons home featuring 4 spacious bedrooms, with 4 full bathrooms and 1 half bathroom. Only 7 minutes from the villages of East Hampton and Sag Harbor, its perfectly located for your Hamptons experience. The bright & open layout is an inviting space for unwinding after the beach. Outdoor living is equally impressive, with a large deck, landscaped gardens and a pool. Set on a peaceful tree-lined cul-de-sac, this Hamptons retreat is ideal for year-round fun

Location · Family · Comfort

East Hampton Secluded Escape with Gunite Pool

Elegantly furnished 4 bedroom house on lushly landscaped grounds, fewer than 5 minutes from the heart of East Hampton Village. This home is ideal for outside living, featuring a gunite, in-ground salt-water pool and stone patio. The interior is bright and spacious, accented by minimalist yet warm furnishings. Common living areas include a large family room with TV, large dining room with gas fireplace, and a large eat in kitchen. Rental registry HMT23-10468

Value · Family · Check-in

Close to all! Peaceful Heated Pool! *Month

Village Fringe, Close to All, Comfortable 3+ bedroom, 2 Bath log home w/ *Heated pool (*heat option May - Sept). Sun filled.. Located on quiet cul-de-sac close to Ocean Beaches & EH Village! Includes *Pool (Open 5/22 ) w/ outdoor shower & changing area. Relax in teak furniture / hammock after a swim in the 20x40 *pool! Peaceful setting. All amenities one would expect. High speed wireless internet 3 Smart TVs. Monthly Rental Registration # 20-1005.

Value · Location · Biking

¤¤¤ Wonderful retreat on 4 acres with pool ¤¤¤

Private, calming, and stylish Hamptons retreat—the ultimate escape from the city. Enjoy an inviting swimming pool from the surrounding hammock, lounge chairs, and swing. The best of indoor-outdoor living is steps away on the wraparound deck featuring an outdoor kitchenette with BBQ, a large outdoor dining table with seating for 12, and an outdoor gas-powered fireplace. All this against the backdrop of 4 acres of private forest greenery.

Value · Family · Air conditioning

Tasteful Hampton 4 Bedroom w Heated Pool EH / Sag

Nestled on a serene half acre, this contemporary, designer-updated residence provides an idyllic Hamptons retreat. With 4 delightful bedrooms, 3.5 sleek bathrooms, and a pool amidst mature landscaping, you're promised a calming respite. We kindly ask that you familiarize yourself with the detailed disclosures, & guidelines. We maintain a strict policy against events, parties, and smoking. our home and property grouds are smoke-free.

Family · Location · Check-in

East hampton 3 bedroom home w/ pool great location

Welcome to your hamptons summer home! Amazing location 5 minutes from both Sag Harbor and East Hampton towns and 10 minutes to Bridge Hampton. Beautifully landscaped backyard with heated pool and bbq. The primary bedroom includes a king bed, the 2 secondary bedrooms have queen beds. Open floor plan with kitchen and dining room flowing to the backyard is perfect for indoor/outdoor lunch and dinners. 2 full bathrooms and central air.

Family · Location · Hospitality