Holiday rentals in Sag Harbor

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Top-rated holiday rentals in Sag Harbor

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Guest favourite

Home in Sag Harbor

4.97 out of 5 average rating, 123 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

$709 SGD per night

Guest favourite

Flat in Sag Harbor

4.94 out of 5 average rating, 134 reviews

Whaling Captain Pierson's Cottage

Whaling Captain Pierson's Cottage is at a waterfront property. A unique environmental experience, nestled in nature but only a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only cottage offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets and a private low-tide beach. (See my reviews from my other listings entitled, "Whaling Captain Pierson's Apartment" and "Whaling Captain Pierson's Apartment TOO".)

28 Aug – 4 Sep

$905 SGD per night

Guest favourite

Cottage in Sag Harbor

5.0 out of 5 average rating, 29 reviews

Luxury Gem At The Heart of Sag Harbor Village

An impeccably renovated, luxury cottage at the heart of Sag Harbor village. Walkable within minutes to the downtown shops, restaurants, marinas and local beach! In one of the most coveted historic streets, enjoy this two-bedroom house, its large living & dining rooms, two fireplaces, designer kitchen (and latest appliances). Countless details and gorgeous wide planked floors, mixed with technology throughout the house. The private backyard has a brick patio, landscaped garden and outdoor shower.

23–30 Jun

$1,164 SGD per night

Guest favourite

Guest suite in Sag Harbor

4.88 out of 5 average rating, 310 reviews

Artists Sag Harbor Village Retreat

January special -book second night for $125! This light and spacious Sag Harbor Village studio apartment is a 10 minute walk from historic Main St. 5 minutes to Village beach. French doors open onto outdoor sitting area. Ideal for a fall or winter visit to explore the area during the quieter season. Main Street is lively and all restaurants are open. Central heat & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking. Fully self contained and private.

14–21 Sep

$360 SGD per night

Guest favourite

Cottage in East Hampton

5.0 out of 5 average rating, 28 reviews

Storybook Cottage Seconds to East Hampton Village

Beach Cottage at edge of East Hampton Village. This fresh and bright cottage with three bedrooms and two new bathrooms is a compact and convenient jewel box with everything you'd expect in the Hamptons - including a beautiful pool with built-in hot tub. Just blocks from the heart of East Hampton on a quiet no-traffic cul-de-sac, not far from beach, shopping, dining and train... sparkling kitchen with new 'retro style' appliances, gleaming hardwood floors throughout, and a cozy front porch.

23–30 Oct

$743 SGD per night

Guest favourite

Flat in Sag Harbor

4.98 out of 5 average rating, 131 reviews

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!

4–11 Oct

$470 SGD per night

Guest favourite

Guest suite in Sag Harbor

4.89 out of 5 average rating, 128 reviews

Old World Charm Private Suite with Own Entrance

***PLEASE ASK ME ABOUT LONGER TERM DISCOUNT*** Private separate suite inside historic village home with own private separate entrance with private bath and kitchenette in modernized 1790 sailor’s home featured in House Beautiful Magazine. Charming historic original detail. Two minute walk to Bay for best sunset, Main Street and Jitney stop in Sag Harbor Village also steps away. Please also note: extra room for up to 2 people is also available in the main house, please inquire.

2–7 Jan

$390 SGD per night

Guest favourite

Home in Sag Harbor

4.84 out of 5 average rating, 45 reviews

Modern Home in Sag Harbor, NY

Set on high ground sits a sleek modern home, Published Richard Moger Modernist built the house for himself in the iconic Amagansett-style beach cottage of Charles Gwathmey. With over 2 acres of privacy is a perfect study in stylish modern design. The open plan, and floor to ceiling glass floods the home with light, showcasing the beautiful natural surroundings. Including a monthly tick and mosquitos professional treatments An updated velvety grey hues hot tub and jacuzzi

11–18 Sep

$1,020 SGD 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

10–17 Dec

$263 SGD per night

Guest favourite

Home in Sag Harbor

4.95 out of 5 average rating, 129 reviews

Luxury Private King Suite + 2 Floor Living Space

Your modern, spacious, sparkling clean guest home has 2 private floors and a private entrance. The bedroom provides luxury and calm as light from the green trees filters in. Watch movies & chill in your living room complete with kitchenette, wine cooler, powder room and adjoining dining space. You’re in a peaceful neighborhood facing a land forest preserve, 5 minutes from bay beaches and the plethora of farm fresh, organic Sag Harbor eateries.

18–25 Oct

$597 SGD per night

Guest favourite

Flat in Sag Harbor

4.98 out of 5 average rating, 117 reviews

Sag Harbor Retreat

Experience the many wonderful things the Hamptons has to offer in the Summer in centrally-located Sag Harbor. Our place is a professionally-decorated luxury apartment with its own entrance, yard and two parking spaces. This home-away-from-home is an immaculate and well-appointed retreat located in Sag Harbor. Great for couples and solo adventurers. Close to Sag Harbor's Main Street with abundant recreational activities, shopping and restaurants.

9–16 Oct

$1,018 SGD per night

Guest favourite

Flat in Sag Harbor

4.95 out of 5 average rating, 83 reviews

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR

Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool .

12–19 May

$368 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Sag Harbor holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Sag Harbor's top sights

Baron's Cove59 locals recommend

LT Burger62 locals recommend

Sag Pizza59 locals recommend

Page at 63 Main40 locals recommend

Dockside Bar & Grill61 locals recommend

American Hotel124 locals recommend

Other great holiday rentals in Sag Harbor

Guest favourite

Home in Sag Harbor

4.96 out of 5 average rating, 26 reviews

Sag Harbor Chic Mid-Century retreat.

3–10 May

$734 SGD per night

Guest favourite

Home in Sag Harbor

4.99 out of 5 average rating, 67 reviews

Luxurious All-Season Oasis close to Sag Harbor Village

26 Apr – 3 May

$1,520 SGD per night

Guest favourite

Cottage in Sag Harbor

4.94 out of 5 average rating, 51 reviews

Steps to the Beach - Designer Cove House Cottage

3–10 Sep

$1,095 SGD per night

Guest favourite

Home in Sag Harbor

5.0 out of 5 average rating, 92 reviews

Secluded Modern Beach Style House

1–8 Nov

$1,162 SGD per night

Guest favourite

Home in Sag Harbor

4.89 out of 5 average rating, 70 reviews

Sag Harbor Wonder, 3 bedroom 2 Bath & Heated Pool

25 Sep – 2 Oct

$1,339 SGD per night

Guest favourite

Cottage in Bridgehampton

5.0 out of 5 average rating, 50 reviews

Bridgehampton Cottage Close to Town, South of HWY

21–28 Apr

$517 SGD per night

Guest favourite

Home in Sag Harbor

4.96 out of 5 average rating, 24 reviews

The Hamptons Casita: Modern Elegance Meets Cozy

29 Apr – 6 May

$607 SGD per night

Guest favourite

Home in Sag Harbor

5.0 out of 5 average rating, 9 reviews

Sunny Sag Harbor Retreat

28 Apr – 5 May

$864 SGD per night

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Quick stats about holiday rentals in Sag Harbor

Total rentals	270 properties
Rentals with a pool	130 properties have a pool
Pet-friendly rentals	110 properties allow pets
Family-friendly rentals	210 properties are a good fit for families
Total number of reviews	6.3K reviews
Nightly prices starting at	$123 SGD before taxes and fees

Holiday rentals in Sag Harbor

Top-rated holiday rentals in Sag Harbor

Home in Sag Harbor

Flat in Sag Harbor

Cottage in Sag Harbor

Guest suite in Sag Harbor

Cottage in East Hampton

Flat in Sag Harbor

Guest suite in Sag Harbor

Home in Sag Harbor

Guest suite in Sag Harbor

Home in Sag Harbor

Flat in Sag Harbor

Flat in Sag Harbor

Holiday rentals for every style

Houses

Cottages

Flats

Popular amenities for Sag Harbor holiday rentals

Stay near Sag Harbor's top sights

Other great holiday rentals in Sag Harbor

Home in Sag Harbor

Home in Sag Harbor

Cottage in Sag Harbor

Home in Sag Harbor

Home in Sag Harbor

Cottage in Bridgehampton

Home in Sag Harbor

Home in Sag Harbor

Quick stats about holiday rentals in Sag Harbor

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Destinations to explore