Sag Harbor vacation rentals

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Top-rated vacation rentals in Sag Harbor

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Guest favorite

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.

Nov 24 – Dec 1

G$108,560 GYD per night

Guest favorite

Apartment 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".)

Mar 4 – 11

G$81,496 GYD per night

Guest favorite

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.

Sep 24 – Oct 1

G$59,611 GYD per night

Guest favorite

Guesthouse in Southampton

4.95 out of 5 average rating, 411 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

Oct 2 – 9

G$66,682 GYD per night

Guest favorite

Home in East Hampton

4.97 out of 5 average rating, 119 reviews

East Hampton (walking distance to village)

Relax by the hot tub and fire pit with local wines or walk to the village for shopping and dining. House is just a few blocks from Serafina and the famous Nick and Toni’s. Complimentary cruiser bikes included to get around town. IGA supermarket is around the corner and gas grill is on site and ready to use. The house is also walking distance to the train station if your coming from Manhattan. The second bedroom features a Murphy Bed that folds out of the wall and over the couch pictured.

Dec 23 – 30

G$145,836 GYD per night

Guest favorite

Apartment 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!

Oct 7 – 14

G$72,064 GYD per night

Guest favorite

Home in Sag Harbor

4.95 out of 5 average rating, 100 reviews

Sag Harbor Village Cottage with 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, and tennis. 10 minute drive to Wolffer & ocean beaches. 4 bedrooms, 2 modern bathrooms and pool with mature landscaping offers a relaxing escape. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking – no exceptions!

May 29 – Jun 5

G$231,415 GYD per night

Guest favorite

Cottage in Southampton

4.97 out of 5 average rating, 99 reviews

Charming Southampton Light filled Cottage

Escape and relax in this beautiful tranquil Southampton retreat! Newly remodeled cottage just blocks from the water. The home is nestled on 1/2acre quiet park-like setting located at the end of a long gravel driveway. Enjoy the private outdoor space with a fire pit, outdoor dining table, new dual BBQ and lounge chairs. Inside, the large dining room table easily sits 8. This stylish Coastal farmhouse has all new beds and furniture. Complete with Wifi, Cable, AC and Nespresso maker!

Sep 26 – Oct 3

G$210,386 GYD per night

Guest favorite

Guest suite in Sag Harbor

4.89 out of 5 average rating, 129 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.

Sep 15 – 20

G$77,704 GYD per night

Guest favorite

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

Dec 14 – 21

G$40,271 GYD per night

Guest favorite

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.

Oct 9 – 16

G$91,568 GYD per night

Guest favorite

Apartment 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.

Oct 24 – 31

G$156,050 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Sag Harbor vacation rentals

Beachfront

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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 vacation rentals in Sag Harbor

Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 585 reviews

Walk to Vineyards, Beaches, Farms & Town

Oct 7 – 14

G$35,599 GYD per night

Guest favorite

Home in East Hampton

4.94 out of 5 average rating, 202 reviews

Private beach Historical House with large property

Nov 20 – 27

G$114,320 GYD per night

Guest favorite

Guesthouse in Hampton Bays

4.96 out of 5 average rating, 145 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

Jan 6 – 13

G$119,649 GYD per night

Superhost

Home in Sag Harbor

4.82 out of 5 average rating, 132 reviews

New! Sag Harbor Village Pool, Hot Tub &Beach House

May 27 – Jun 3

G$211,381 GYD per night

Guest favorite

Apartment in Sag Harbor

4.84 out of 5 average rating, 171 reviews

Pet friendly, artists apartment & guest cabin.

Sep 30 – Oct 7

G$105,822 GYD per night

Guest favorite

Home in Southampton

4.97 out of 5 average rating, 127 reviews

Dream Home with a wonderful heated pool in SH

Apr 30 – May 7

G$51,616 GYD per night

Guest favorite

Apartment in Southampton

4.96 out of 5 average rating, 164 reviews

Sunny Southampton Studio

Aug 20 – 27

G$143,151 GYD per night

Guest favorite

Guest suite in East Hampton

4.96 out of 5 average rating, 142 reviews

Private peaceful poolside Suite close to bch/town

Jun 21 – 28

G$125,716 GYD per night

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Sag Harbor cottage rentals

Guest favorite

Cottage in East Hampton

4.98 out of 5 average rating, 263 reviews

Carriage House - Cottage in East Hampton Village

Jan 7 – 14

G$64,590 GYD per night

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 163 reviews

Secluded Southampton Cottage w/Pool & Spa

Sep 23 – 30

G$212,885 GYD per night

Guest favorite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Nov 20 – 27

G$155,628 GYD per night

Guest favorite

Cottage in East Hampton

4.89 out of 5 average rating, 123 reviews

East Hampton Fisherman’s Cottage with Secret Room

Jan 21 – 28

G$59,334 GYD per night

Superhost

Cottage in Laurel

4.76 out of 5 average rating, 273 reviews

North Fork Cottage

Mar 26 – Apr 2

G$37,268 GYD per night

Guest favorite

Cottage in Montauk

4.91 out of 5 average rating, 515 reviews

Montauk Oceanview

Nov 2 – 9

G$46,815 GYD per night

Guest favorite

Cottage in Hampton Bays

4.9 out of 5 average rating, 109 reviews

Hamptons cottage just steps from the beach.

Oct 27 – Nov 3

G$90,158 GYD per night

Superhost

Cottage in Cutchogue

4.69 out of 5 average rating, 187 reviews

Lovely 2 BR Beach House No. Shore

Mar 29 – Apr 5

G$41,229 GYD per night

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Beach cottage rentals in Sag Harbor

Guest favorite

Cottage in Southold

4.9 out of 5 average rating, 151 reviews

Comfortable Cottage on the Great Pond near beach.

Mar 10 – 17

G$59,397 GYD per night

Guest favorite

Cottage in Montauk

4.91 out of 5 average rating, 138 reviews

Montauk Cottage Escape

Feb 15 – 22

G$84,169 GYD per night

Superhost

Cottage in Southampton

4.87 out of 5 average rating, 52 reviews

Charming Southampton Beach Cottage 3 bedroom

May 4 – 11

G$76,699 GYD per night

Guest favorite

Cottage in Sag Harbor

4.98 out of 5 average rating, 49 reviews

Charming Scandinavian Inspired Beach Cottage

Aug 15 – 22

G$215,453 GYD per night

Guest favorite

Cottage in Sag Harbor

4.95 out of 5 average rating, 86 reviews

Cozy Cottage by the Sea Sag Harbor

Dec 29 – Jan 5

G$191,397 GYD per night

Guest favorite

Cottage in Hampton Bays

4.95 out of 5 average rating, 37 reviews

Hamptons Cottage.

Apr 24 – May 1

G$51,608 GYD per night

Guest favorite

Cottage in Mattituck

4.97 out of 5 average rating, 31 reviews

Cozy Cottage By The Bay, Farms & Vineyards!

Oct 19 – 26

G$62,655 GYD per night

Superhost

Cottage in Shelter Island

4.76 out of 5 average rating, 45 reviews

Large Waterfront Cottage on Historic Estate

Jul 7 – 14

G$116,729 GYD per night

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Quick stats about vacation 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
G$18,806 GYD before taxes and fees

Frequently Asked Questions

What types of vacation rentals are available in Sag Harbor?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Sag Harbor. From over 200 house rentals to over 10 cottage rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Sag Harbor?
Yes! Work meets play with ease at over 140 vacation rentals in Sag Harbor featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Sag Harbor?
Four-legged friends are welcome in Sag Harbor. Choose from more than 110 vacation rentals for guests traveling with pets.
Are there Sag Harbor vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 130 vacation homes with pools in Sag Harbor, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in cottage rentals in Sag Harbor?
Experience the best of Sag Harbor with our cottage rentals, starting at about $190 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Sag Harbor have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Sag Harbor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Sag Harbor have a gym?
Absolutely! We offer over 30 house rentals with a gym in Sag Harbor. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Sag Harbor have a bbq area?
Absolutely! We offer over 120 house rentals with a bbq area in Sag Harbor. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Sag Harbor?
Sag Harbor has more than 180 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Sag Harbor?
Enhance your stay in our House Rentals with the most popular amenities: over 120 homes with a bbq area, over 200 homes with wifi, over 30 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.

Sag Harbor vacation rentals

Top-rated vacation rentals in Sag Harbor

Vacation rentals for every style

Cottages

Apartments

Houses

Popular amenities for Sag Harbor vacation rentals

Stay near Sag Harbor's top sights

Other great vacation rentals in Sag Harbor

Guest suite in Cutchogue

Home in East Hampton

Guesthouse in Hampton Bays

Home in Sag Harbor

Apartment in Sag Harbor

Home in Southampton

Apartment in Southampton

Guest suite in East Hampton

Sag Harbor cottage rentals

Cottage in East Hampton

Cottage in Southampton

Cottage in Riverhead

Cottage in East Hampton

Cottage in Laurel

Cottage in Montauk

Cottage in Hampton Bays

Cottage in Cutchogue

Beach cottage rentals in Sag Harbor

Cottage in Southold

Cottage in Montauk

Cottage in Southampton

Cottage in Sag Harbor

Cottage in Sag Harbor

Cottage in Hampton Bays

Cottage in Mattituck

Cottage in Shelter Island

Quick stats about vacation rentals in Sag Harbor

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

What types of vacation rentals are available in Sag Harbor?

Are there vacation rentals with a dedicated workspace in Sag Harbor?

Are there pet-friendly vacation rentals in Sag Harbor?

Are there Sag Harbor vacation rentals on Airbnb with pools?

How much does it cost to stay in cottage rentals in Sag Harbor?

Do cottage rentals in Sag Harbor have wifi?

Do house rentals in Sag Harbor have a gym?

Do house rentals in Sag Harbor have a bbq area?

Are there family-friendly house rentals in Sag Harbor?

What are the most popular amenities for House Rentals in Sag Harbor?

Destinations to explore