
Family-friendly holiday rentals in Wainscott
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Top-rated family-friendly rentals in Wainscott
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Silver House: 3BR Home with Private Beach Access
Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Detached bungalow w/ private bath
Cozy, simple living, in separate guest house w/ use of amenities (shared with our family of 4) including sauna & hot tub. The bungalow/guesthouse features a Queen bed, its own private bathroom (shower), small kitchenette (countertop oven, Keurig coffee maker & small fridge) and loveseat for relaxing. There is a dedicated separate outdoor seating area for 2 guests. 2 Adult guests ONLY, no children due to size of guesthouse and proximity to the pool. Please NO pets allowed since owners have pets

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 / restaurants / Havens beach, and 10 mins to Bridgehampton. Location, location! And Views! - 3 Beds and 2.5 baths + pool house - Pool house with twin sofa bed + full bath - 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

Southampton Charmer, 5 bedrooms w pool - Location
This 5-bedroom home boasts en-suite baths and elegant furnishings. The gourmet kitchen features marble countertops and stainless steel appliances, leading to a dining area. The lower level includes a spacious seating area and a game room with toys. The second floor houses a master suite with stunning views and three additional en-suite bedrooms. Located minutes from the village center, with restaurants, shops, and beaches nearby. A heated pool invites you to relax and enjoy the comfort of home.

Calf Creek Cottage (Water Mill/Bridgehampton)
Enjoy the peaceful seclusion of this charming, updated 3 bedroom, 2 bath cottage located on a private, acre-sized flag-lot south of the highway right on the border of Water Mill and Bridgehampton. Each bedroom (1 king, 2 queen) features ample closet space and new smart TVs . The new, fully-stocked kitchen, propane BBQ, outdoor dining table for 8, outdoor shower and spa with lounge furniture, and wood burning fireplace make it the perfect getaway for either summer or the winter season. Pets OK.

East Hampton Village Fringe, Renovated with Pool
This remarkable East Hampton home, nestled along a quiet cul-de-sac, is just moments from shopping, restaurants, and ocean beaches. The residence features an abundance of natural light, crisp neutral color tones, and tall, pitched ceilings that enhance the sense of space. The calming, heated pool provides a perfect retreat for relaxation. Please review our disclosures and house manual to ensure this home meets your needs and expectations. We want to make sure it’s the perfect fit for you.

Updated apartment in historic village home
Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

Serene East Hampton Escape - Stars Forest Sauna
A luxuriously curated woodland escape with massive pool, outdoor dining living and play areas, 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 a french privacy door, a freestanding soaking tub, and a chef’s kitchen with dining table for ten or more.

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool
Situated on a half-acre of land, this classic shingle cottage with brand new designer interiors offers the ideal Hamptons getaway. Located in the picturesque village of Sag Harbor, less than a mile from town, bay beaches. 10 minute drive to Wolffer & ocean beaches. 3 bedrooms, 2 modern bathrooms and heated pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

Harbor Heights
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).

Private central cozy king suite 2 baths fireplace
Beautiful, bright, spacious King suite w fireplace, two en-suite bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book or movie. The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

Cheerful East Hampton home with Pool
Situated off of a quiet lane on one and a half-acres of land, this amazing residence offers a peaceful and quiet Hamptons getaway. The home consists of 4 wonderful bedrooms, 3.5 modern bathrooms, a heated pool & mature landscaping. Additionally, please read my disclosures and "rules". Not a party house. No Events, parties & No smoking will be permitted. The house is beautiful, tranquil and very comfortable. THANK YOU!
Popular amenities for Wainscott family-friendly rentals
Family-friendly home rentals with a hot tub

Private Oasis W/Stunning Vinyard and Pool Views

Greenport Village walking distance to all

4 BR/3BA Quiet Pool Home

Montauk Waterfront Condo w/ Sunset Views

Chic East Hampton 7 Bedroom, 7 Bath, heated Pool

Brand new house with an all year round hot tub.

East Hampton Oasis - Pool and Hot Tub

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My
Family- and pet-friendly home rentals

PICTURE PERFECT SOUTHAMPTON HOME-

Private & Pristine with Pool and Kid’s Playard

Modern Farmhouse Steps to Beach & Love Lane

Classic Southampton Village Home w/ Pool

Southampton apt walk to village

Peaceful getaway in the Hamptons

Wake up to Stunning Views at a Serene Waterfront Haven

Contemporary East Hampton 4 Bedroom, Pool
Family-friendly home rentals with a pool

Storybook Cottage Seconds to East Hampton Village

4BR Heart of the Hamptons w/pool

Hampton Oasis with private Tennis, Pool, Theater

Central Private Bridgehampton

Delightful Sag Harbor Home w Pool

Sag Harbor Chic 4 Bedroom Saltwater Pool

Renovated Southampton Home+Pool

Cheerful 3 bed-3bath beach cottage home with pool
When is the best time to visit Wainscott?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $960 SGD | $1,227 SGD | $1,224 SGD | $1,152 SGD | $1,281 SGD | $1,537 SGD | $1,954 SGD | $2,049 SGD | $1,316 SGD | $1,024 SGD | $1,024 SGD | $1,023 SGD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 15°C | 21°C | 24°C | 23°C | 19°C | 13°C | 8°C | 3°C |
Quick stats about holiday rentals that are family-friendly in Wainscott

Total holiday rentals
Explore 340 holiday rentals in Wainscott

Nightly prices starting at
Wainscott holiday rentals start at $205 SGD per night before taxes and fees

Verified guest reviews
Over 4,170 verified reviews to help you choose

Pet-friendly holiday rentals
Find 160 rentals that welcome pets

Holiday rentals with a pool
300 properties feature pools

Rentals with dedicated workspaces
210 properties have a dedicated workspace

Wifi availability
340 of Wainscott holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wainscott rentals

4.9 Average rating
Wainscott stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a fireplace Wainscott
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- Family-friendly rentals Suffolk County
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- Family-friendly rentals United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Ocean Beach Park
- Long Island Aquarium
- Mohegan Sun
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- Powder Ridge Mountain Park & Resort
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