
House holiday rentals in Wainscott
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Top-rated house rentals in Wainscott
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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.

Private beach, fully updated house, on 2 acres.
Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

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

Serene + private, 1 block to waterfront dining
Come enjoy this chic, serene private home; located just 1 block to waterfront dining and minutes to Main St.! Bask in your Hamptons oasis at this half-acre property. Enjoy outdoor/indoor living, hang on the porch during Summer, swim in your pool all day + night, spark up the BBQ + firepit under the starry sky! Stroll 1 block to waterfront dining + cafe to enjoy the most magnificent sunsets in the area, You'll be 5 minutes to Main St. of East Hampton + Amagansett, restaurants, beaches + more!

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

Explore the Water & Woods at a Relaxing Retreat
No AI used in these photos! Flick through records under soaring ceilings and hang out in the year-round hot tub at this East Hampton open-plan retreat. Unwind in the wooded backyard, take a dip in the pool or spa, detox in the sauna, grill on BBQ, relax in the movie-theatre seats to watch a film, then snuggle up to fireplace or firepit before drifting to sleep in super comfy beds. Minutes to village, beaches and hiking trails. Terrific for families & friends looking for a relaxing getaway.

East Hampton Oasis - Pool and Hot Tub
Nestled at the end of a private road in the Springs section of East Hampton, this classic Hamptons home will keep you and your friends/family entertained. Living room with sonos sound system, kitchen, 3 bedrooms, 2 bathrooms, outdoor living area with lounge chairs, a bbq, bar, pool and hot tub. All 3 bedrooms have AC. Towels and linens provided. Washer/dryer available. CLOSE TO BEACH AND EH VILLAGE. The pool is open May 5 through October 5. The hot tub remains open year round.

Sunny & Serene Private Cottage near Downtown EH
Our lovely one-bedroom cottage sits on a quiet lane 3/4 of a mile from downtown East Hampton. The cottage is light and bright, with whitewashed walls, vaulted ceilings and skylights, lots of windows and beautiful minimalist décor. It's an incredibly peaceful place to wake up in the morning, with a gorgeous green yard right outside the many bedroom windows. Every bay and ocean beach around East Hampton is 5-10 minutes away and Nick and Toni's is less than a 10 minute walk.

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).

The Cooper-Burke House
Many Main Street restaurants such as the American Hotel, Lulu's, Page 63, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.

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!

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.
Popular amenities for house rentals in Wainscott
House rentals with a pool

3 BR/Pool. Walk to Beach & Town!

Private & Pristine with Pool and Kid’s Playard

Modern East Hampton Home w/ Heated Saltwater Pool

Southold waterfront 4 bed, pool open til October

Classic Southampton Village Home w/ Pool

Secluded Farmhouse - Studio Apartment Style Unit

Hamptons Modern Retreat NEW CONS

Luxury Hamptons Home with Heated Saltwater Pool
Weekly house rentals

Breathtaking Sag Harbor 5 bed 6 bath-Heated Pool

Southampton Village Newly Built Gem

Hampton Oasis with private Tennis, Pool, Theater

Charming Village Cottage

Wake up to Stunning Views at a Serene Waterfront Haven

Secluded Luxury: New Gunite Pool, Walk to Bay

Renovated Southampton Home+Pool

Scandinavian Cottage
Private house rentals

Cozy East Hampton Getaway

Designer Home w/ Heated, Salt-Water Pool

Charming Sag Harbor Escape!

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

Spectacular Southampton Retreat!

Hamptons Sanctuary - luxurious and secluded.

Perfect Beach Home in Sag Harbor

Sunny, walk to beach, large pool
When is the best time to visit Wainscott?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $912 SGD | $1,136 SGD | $1,170 SGD | $1,024 SGD | $1,213 SGD | $1,468 SGD | $1,838 SGD | $1,920 SGD | $1,263 SGD | $997 SGD | $918 SGD | $1,069 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 house rentals in Wainscott

Total holiday rentals
Explore 340 holiday rentals in Wainscott

Nightly prices starting at
Wainscott holiday rentals start at $126 SGD per night before taxes and fees

Verified guest reviews
Over 4,770 verified reviews to help you choose

Family-friendly holiday rentals
320 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 150 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 patio Wainscott
- Rentals with outdoor seating Wainscott
- Rentals with beach access Wainscott
- Rentals with a firepit Wainscott
- Fitness-friendly rentals Wainscott
- Rentals with a washing machine and dryer Wainscott
- Rentals with a hot tub Wainscott
- Luxury rentals Wainscott
- Rentals with pools Wainscott
- Pet-friendly rentals Wainscott
- Family-friendly rentals Wainscott
- Rentals with a fireplace Wainscott
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