Family-friendly holiday rentals in Wainscott

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Top-rated family-friendly rentals in Wainscott

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Guest favourite

Home in Sag Harbor

4.97 out of 5 average rating, 124 reviews

Relax into Coastal Life at a Sun-Drenched Sag Harbor Home

Take a bike ride to Havens Beach and feel the sand in your toes. Walk to explore the shops, restaurants and bars on the quaint Main Street of Sag Harbor. Repair to your sun drenched home away from home to enjoy a relaxed meal alfresco on the deck. Unwind under the umbrellas on the expansive deck surveying the private fenced in backyard. Take in all the amenities of a newly renovated home situated in the Hampton - recent updates include a furnished basement, ping pong table, smart TVs and sound system. Extra touches include beach towels, beach chairs, bikes, cooler, games and more. This beautifully renovated 3 BR, 2 Bath home is situated on a quiet street, with a fenced half acre yard. It is located less than a mile to the shops, bars and restaurants of Main Street and the Hampton Jitney stop with service to NYC. The open floor plan boasts an abundance of natural light with 4 skylights and large windows to bring the outdoors in. Brand new appliances, custom kitchen cabinets, large center island with bar stools are perfect for hosting friends & family. Central AC/forced air heating controlled by the Nest ensure your complete comfort. The master BR features a king bed and ensuite Bath with custom tile shower. The guest BRs have a queen bed and full bed respectively and share the hall bathroom with tub/shower. The large deck runs the length of the home and is perfect for al fresco dining & entertaining. Totally furnished with everything you need to enjoy yourself from the second you enter the home! We have four brand new adult bikes, helmets and locks for your enjoyment. Explore the village, bike to the beach or get some exercise while you're here. If you prefer to stay in, you'll find a games console / DVD player in the front room with a good selection of games and movies. Additionally, we provide 4 beach chairs, beach towels and a small cooler for your use. Enjoy! Guests have access to the entire house, backyard, deck, garage and driveway parking. We can be reached via cell or email and are very responsive. We will also have a friend who is local to the area who will be able to assist with any issues. Sag Harbor is the coolest, most authentic town in the Hamptons. Home to household names, the town retains its small-town charm and rustic maritime vibe. Browse the artsy, eclectic stores and strike up conversations in the coffee shops and local bars. Sag Harbor is a quaint, walkable town on the wharf with great restaurants and bars. The house is located less than a mile's walk into the main street. Beaches are accessible via bike or car. The Jitney stop from Manhattan is located on Main Street less than a mile from the house. There are taxis in the area available via phone for pick up. We provide four adult bikes, helmets and locks for your use.

24 Nov – 1 Dec

$939 NZD per night

Guest favourite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Enjoy the designer kitchen with all new appliances, as well as a brand new bathroom, updated bedrooms and outdoor shower. This chic 2-bedroom, 1-bathroom home, which can sleep up to 5, has been designed with an eye for detail, style and relaxation. The master bedroom enjoys a queen sized bed that's perfect for 2 adults. The second bedroom can accommodate up to 3 people with a double bed for two people, and a single bed for one person. Only 80-miles from Manhattan, a 90-minute drive and close to the towns of Jamesport, Southold and Greenport, The Beach Cottage is the perfect summer escape. Stay on the property for swimming, paddle boarding, beach walks and BBQs or venture out to enjoy all the North Fork has to offer. Wine tasting at the French run winery Croteaux, lunch at the world class North Fork Table and Inn, shop at the many Organic Farms or explore the charming historic seaport village of Greenport, all short drives from the cottage. Upon request, Pets are allowed, for an extra fee of $200 per stay. Guests have access the entire property, including a private path to the beach. This stylish retreat is nestled on a private Soundfront beach at the end of a 7-acre property. Wine tasting at Croteaux, lunch at world-class North Fork Table and Inn, and the historic seaport village of Greenport are all within a short drive. The closest Jitney stop is Aquebogue or Riverhead. I am an Australian born designer that lives in NYC and has been renovating homes for the past several years. Our Flatiron loft in NYC was featured in Dwell Magazine, I designed the Upper West Side apartment for the founder & CEO of Soul Cycle, and my husband and I recently renovated our family's weekend beach house on the North Fork. I have a passion for turning houses into homes by bringing the clean, breezy and natural aesthetic, inspired by my homeland in Australia.

10–17 Jan

$1,303 NZD per night

Guest favourite

Home in East Hampton

4.94 out of 5 average rating, 202 reviews

Private beach Historical House with large property

Entire three-story house. 3 large bedrooms and 3 FULL BATHROOMS on a very private, 2+acre wood lot on the bay in Historical East Hampton with private beach access. Fully renovated in 2018 with modern amenities while preserving the original charm. A/C and heating. Private upper floor with bedroom + sitting area for office and extra sleeping. Modern kitchen with island that opens to living room with fireplace. Walk through the secluded backyard to enjoy the amazing sunsets. Ideal for fishing.

10–17 Jun

$1,201 NZD per night

Guest favourite

Home in East Hampton

4.87 out of 5 average rating, 188 reviews

Heated Saltwater Pool, Walk to Beach, Dog Friendly

Meticulously cleaned home. Tranquil family neighborhood in historic artist's beach community. Wood burning fireplace. Private fenced-in backyard . Heated saltwater pool in summer. Half mile to private bay beach, bike great trails & savor delicious meals prepared in fully equipped kitchen. Don’t miss Clearwater Beach's stunning sunset. Easy living home.Welcoming to all respectful families & guests.East Hampton's best restaurants are nearby. Smoke free.Small dogs permitted.Rental Registry 23-625.

23–30 Oct

$542 NZD per night

Guest favourite

Apartment in Sag Harbor

4.92 out of 5 average rating, 133 reviews

Whaling Captain Pierson's Apartment TOO

Whaling Captain Pierson's Apartment TOO is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment and Whaling Captain Pierson's Cottage)

3–10 Jun

$1,076 NZD per night

Guest favourite

Home in East Hampton

4.92 out of 5 average rating, 128 reviews

Heated pool, games room, near beach, kid-friendly

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (open 04/19 - additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool, shoot hoops, or take a 15 minute walk to the private (and empty) bay beach where you can use my paddle board. Or drive to the famous Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg 22-1590 Local taxes included

23–30 Oct

$1,247 NZD per night

Guest favourite

Home in Greenport

4.92 out of 5 average rating, 423 reviews

Blue Bay Dream

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

15–22 Jan

$231 NZD per night

Guest favourite

Guest suite in Sag Harbor

4.95 out of 5 average rating, 188 reviews

Cedar Haven In Sag Harbor

This is a large one room studio apartment with private entrance and ensuite bathroom. The unit is private and closed off from the host’s house. The large main room has a queen bed, and a spacious seating area that includes chairs as well as a comfy leather couch. PLEASE NOTE: One night stays are welcomed but there is a higher rate: IN season, (June 1 - Oct 31) the ONE NIGHT RATE is $375 OFF season, (mid Oct - end of May) the ONE NIGHT RATE is $300

28 Aug – 4 Sep

$464 NZD per night

Guest favourite

Guest suite in East Hampton

4.89 out of 5 average rating, 222 reviews

Private Cozy Cottage with Pool / Private Beach

**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

9–16 Oct

$468 NZD per night

Guest favourite

Home in Sag Harbor

4.85 out of 5 average rating, 250 reviews

Exclusive Sag Harbor Compound

A private country compound in heart of Sag Harbor. House just gut renovated with all top of line (all Wolf and Subzero appliances). The main house is 3 bedrooms, 3.5 bath main house PLUS separate large guest cottage (with a King bed, bar fridge, and full bathroom). Gunite pool (i.e., salt chlorinated which makes it feels like clean freshwater). Walk to town, bay beach, public tennis courts, 1000 acre nature preserve.

4–11 Dec

$945 NZD per night

Guest favourite

Guest suite in Cutchogue

4.88 out of 5 average rating, 587 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

15–22 Oct

$305 NZD per night

Guest favourite

Cottage in East Hampton

4.89 out of 5 average rating, 123 reviews

East Hampton Fisherman’s Cottage with Secret Room

This renovated cottage is located just a few minutes from East Hampton Village and is walking distance to Three Mile Harbor. This light filled home features wood flooring throughout, inviting living room with vaulted ceiling, an updated kitchen, two bathrooms (one with a secret entrance!) and a side yard with a brick patio, outdoor shower and hammock.

17–24 Dec

$524 NZD per night