Holiday rentals in Sag Harbor

4.94 out of 5 average rating, 154 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".)

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.

5 out of 5 average rating, 9 reviews

Oh Buoy! Charming Cottage Steps to Beach | Firepit

This nautical-inspired "tiny house" cottage in beloved Sag Harbor is the perfect spot for a single or couple to enjoy the Hamptons beachy lifestyle. The sunny living room features a sitting area and stylish kitchenette. The bedroom has a full sized-bed and en suite bath. Fully appointed for your stay, just bring your bathing suit! Outside is your own little deck with a bistro table and a fire pit / BBQ area, and my own house is just across the lawn so I'm readily accessible! 1 parking spot.

4.98 out of 5 average rating, 176 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.

4.93 out of 5 average rating, 121 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 from May till end of the September .

4.99 out of 5 average rating, 70 reviews

Cottage in Sag Harbor

Charming Scandinavian Inspired Beach Cottage

Steps from Circle Beach. Charming 2 bed/ 2.5 bath w a separate studio w a twin daybed and 1/2 bath, outdoor shower, large outdoor entertaining patio with a grill. The master bed has a queen bed and the bunk room has a full bed w a twin on bed on top. Located in the cute beach community of Pine Neck, this is Sag Harbor's best kept secret! Chef's kitchen is equipped with top of the line appliances and gadgets. The master bathroom features a clawfoot soaking tub.

Guest suite in Sag Harbor

4.9 out of 5 average rating, 356 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, 268 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.

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.

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Houses

A space that's all yours, with room for everyone

Popular amenities for Sag Harbor holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Sag Harbor

5 out of 5 average rating, 44 reviews

Home in Noyack

Sag Harbor Chic Pool Grill Gym Outdoor Shower Dog

CarterRating, 5 stars3 weeks ago

Beautiful home and amazing pool and garden. And great host! Would definitely stay here again.

4.93 out of 5 average rating, 15 reviews

Sag Harbor Historic Village

StephanieRating, 5 stars1 month 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!

4.97 out of 5 average rating, 197 reviews

Sag Harbor home away from home

SueRating, 5 stars6 days ago

We are repeat customers to Fran's house. It is perfect for us. Fran is a wonderful hostess. She is friendly, highly responsive and helpful. The house is pristine and very comfortable. We look forward to coming back year after year. It has everything you could want in a vacation rental.

5 out of 5 average rating, 49 reviews

Apartment in Sag Harbor

Sag Harbor Mona Lisa suite

MattRating, 5 stars9 months ago

I cannot say enough good things about Michael's place. He was amazingly responsive and incredibly generous in how well-equipped the space is - everything is luxurious and the fridge is stocked! For as nice as it looks in the photos, it is even larger, brighter and more welcoming in person.

5 out of 5 average rating, 20 reviews

Cozy Get Away Sag Harbor Village Studio

CassRating, 5 stars10 months ago

H was sooo kind and thoughtful. She kindly welcomed us and offered privacy. H's place was exactly as described and sooo cozy. I hope to return. Thank you so much!

Cottage in East Hampton

4.75 out of 5 average rating, 96 reviews

Spacious East Hampton Getaway with Pool

MariaRating, 5 stars4 weeks ago

Our stay was fantastic from start to finish. The space was exceptionally clean and well-maintained, which made us feel instantly comfortable. Check-in was seamless and clearly communicated, allowing us to settle in quickly without any hassle. The host was incredibly responsive and helpful—always available to answer questions and made sure we had everything we needed throughout our stay. Overall, a smooth and stress-free experience! Definitely will book again in the future!

Guest house in Sag Harbor

4.83 out of 5 average rating, 131 reviews

Sag Harbor Cottage in historic district

DanielRating, 5 stars4 weeks ago

A great little place in Sag Harbor. Comfortable bed, excellent linens and towels. We were only there for sleeping and showers, but Joan responded quickly to our request for a hair dryer. Might be tight for hanging out there, but ideal for us. Very convenient and easy all around.