Holiday rentals in Sag Harbor

4.97 out of 5 average rating, 149 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.

4.94 out of 5 average rating, 156 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".)

5 out of 5 average rating, 52 reviews

Cottage in Sag Harbor

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.

4.96 out of 5 average rating, 156 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

4.98 out of 5 average rating, 179 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!

4.95 out of 5 average rating, 80 reviews

Cottage in Sag Harbor

Steps to the Beach - Designer Cove House Cottage

All new modern interior and exterior furnishings by luxury interior designer. Enjoy fabulous water views on the expansive mahogany deck from this sweet beach cottage that was completely renovated and is a short walk to beautiful Long Beach and just a couple of miles to Sag Harbor's Main St. The home features an open floor plan, cozy gas fireplace, an updated kitchen with stainless appliances and Viking range. Three bedrooms (one with a private office) and an outdoor shower.

Guest suite in Sag Harbor

4.9 out of 5 average rating, 357 reviews

Artists Sag Harbor Village Retreat

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.

4.86 out of 5 average rating, 269 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.

Guest house in Sag Harbor

4.86 out of 5 average rating, 107 reviews

Charming 2BR Cottage, Walk to Town

Beech Tree Cottage is a charming 2-bedroom, 1-bath cottage conveniently located in the peaceful historic district of Sag Harbor, NY. It is a 5-minute walk along the waterfront to Main Street and the center of the village. PLEASE NOTE: We have a 2 night MINIMUM stay for bookings and 3 nights on holiday weekends. Please review our cancellation policy and house rules before making a request.

4.96 out of 5 average rating, 293 reviews

Sag Harbor Cottage, Walk to the Beach!

Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.

4.95 out of 5 average rating, 99 reviews

Sag village, 4 en-suite BRs, hot tub, beach 5 mins

The newly renovated house with 4 spacious bedrooms (all with an en-suite bathroom) is only minutes from the Sag Harbor Village center. The private bayside beach is warmer and safer to swim (especially for kids) than the Atlantic coast. The house could also be a great base for a weekend trip with the Woelffer and Channing Daughters wineries only a short drive away.

5 out of 5 average rating, 17 reviews

Sag Harbor Village Waterfront

Peaceful, waterfront cottage on Upper Sag Harbor Cove, located within Sag Harbor Village. There is a dock with room for a medium size boat or jet skis. House includes three stand up paddle boards, two kayaks, two bicycles an outdoor grill and outdoor dining area and seating.

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Popular amenities for Sag Harbor holiday rentals

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Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Sag Harbor

4.93 out of 5 average rating, 15 reviews

Sag Harbor Historic Village

StephanieRating, 5 stars2 months ago

Hillary’s home was a dream! So clean, stylish and super functional for a sag harbor stay. Walkable to everything in town if you like. Hillary is an awesome host. Very proactive, greets you and shows you the ropes and easily on hand if you need anything but you have totally privacy as well. Had everything we needed and then some. Will definitely be back!

5 out of 5 average rating, 45 reviews

Home in Noyack

Sag Harbor Chic Pool Grill Gym Outdoor Shower Dog

ArianaRating, 5 stars3 days ago

Aniik was delightful, generous, and a matchless host. We planned a mommy-daughter trip to the Hamptons and when an additional two guests were able to come, Aniik was flexible and accommodating. We spoke on the phone and I knew instantly that Aniik is a gem of a person. Her space is beautifully appointed, clean, and spacious. The outdoor space with a salt water pool, umbrellas, and beach chairs made for hours of fun for the three young ladies with us. The house is walkable to a farmstead with wonderful produce, about a 5-10 minute drive to downtown Sag Harbor (charming town with excellent dining and retail), and a short distance driving to Cooper’s Beach in Southampton where we spent an afternoon. Aniik’s instructions were clear and she made her home and amenities accessible to us. Thanks, again, for a beautiful memory filled stay.

Private room in Sag Harbor

4.96 out of 5 average rating, 217 reviews

Sag Harbor Home, Perfect for the Solo Traveler

RohanRating, 5 stars4 days ago

I genuinely cannot speak highly enough of Barbara and her home. She met me at the door for check in, personally took me around the space to show me all the amenities and has many fun books and magazines to read through. Her house is beautiful and tucked away in the woods, so it feels private and has great views, but is also a less than 5 minute drive from downtown Sag Harbor. Barbara was so welcoming and we had some great conversations. It feels like a more personalized, local version of the Hamptons and it was great! And finally, she made an incredible breakfast every morning of fresh fruit, yoghurt and homemade zucchini bread, which was all excellent! Do yourself a favor and stay with Barbara because I will be doing so if possible again!

5 out of 5 average rating, 22 reviews

Cozy Get Away Sag Harbor Village Studio

DouglasRating, 5 stars4 days ago

Despite the elevated prices in Sag Harbor this weekend, likely due to the long Juneteenth holiday, the rate, while high, was well worth it compared to other available options. The property offered a perfect balance of peaceful and private, yet still conveniently close to the heart of town. I would absolutely stay here again and highly recommend it to anyone looking for a relaxing escape that’s still within easy reach of the action.

5 out of 5 average rating, 4 reviews

Sag Harbor Private Spa & Healing Oasis

TatyanaRating, 5 stars10 months ago

We had a very pleasant vacation in Bruce’s beautiful home. Bruce is a great host and very communicative. The place is well equipped with everything to make a comfortable stay. The backyard is fenced and private. We didn’t use a sauna but the pool is very refreshing. It is a short drive to Sag Harbor restaurants and bay beaches. It is a great place to relax and avoid NYC summer heat

4.95 out of 5 average rating, 87 reviews

Cottage in Southampton

Modern Southampton Cottage | Heated Pool & Peloton

EmilyRating, 5 stars1 week ago

Will be back! Cutest spot- both inside and outside were impeccable. Felt very private and was short drive to anything you need. The 2 bathrooms were great for our family, can’t wait to visit again! Really comfortable beds and enjoyable pool and backyard for all.