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

ﺩ.ﺇ1,910 per night

Guest favorite

Apartment in Sag Harbor

4.94 out of 5 average rating, 135 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 1 – 8

ﺩ.ﺇ1,432 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 8 – 15

ﺩ.ﺇ971 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 1 – 8

ﺩ.ﺇ1,228 per night

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 164 reviews

Secluded Southampton Cottage w/Pool & Spa

*Follow Us on Insta @SimmerCottage* This designer-decorated cozy cottage near Southampton Village & a short drive or bike to the beach has a stocked chef's kitchen, cozy living room with wood-burning stone fireplace, 2 SmartTVs, whimsical dining room, 3 bedrooms, one bath & charming sunroom w/reading nooks. The Cottage has central heating/air & is set on a gated 1/2 acre w/hot-tub, outdoor dining for 8 on a stone patio, outdoor string lights, fire pit, gardener's potting station & gas BBQ.

Oct 3 – 10

ﺩ.ﺇ2,683 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 6 – 13

ﺩ.ﺇ1,267 per night

Guest favorite

Home in Sag Harbor

4.94 out of 5 average rating, 101 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 30 – Jun 6

ﺩ.ﺇ3,169 per night

Guest favorite

Guest suite in Sag Harbor

4.89 out of 5 average rating, 130 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.

Aug 1 – 6

ﺩ.ﺇ1,733 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

Jul 11 – 18

ﺩ.ﺇ976 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.

Dec 21 – 28

ﺩ.ﺇ1,553 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 28 – Nov 4

ﺩ.ﺇ2,743 per night

Guest favorite

Home in Sag Harbor

4.85 out of 5 average rating, 250 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.

Nov 17 – 24

ﺩ.ﺇ2,385 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 Burger60 locals recommend

Sag Pizza59 locals recommend

Page at 63 Main40 locals recommend

Dockside Bar & Grill58 locals recommend

American Hotel124 locals recommend

Other great vacation rentals in Sag Harbor

Guest favorite

Home in Southampton

4.9 out of 5 average rating, 215 reviews

PICTURE PERFECT SOUTHAMPTON HOME-

Oct 2 – 9

ﺩ.ﺇ2,114 per night

Guest favorite

Home in East Hampton

4.96 out of 5 average rating, 188 reviews

Ritz-East Hampton Cottage- 5 stars

Jun 16 – 23

ﺩ.ﺇ1,923 per night

Guest favorite

Apartment in Sag Harbor

4.84 out of 5 average rating, 172 reviews

Pet friendly, artists apartment & guest cabin.

Nov 12 – 19

ﺩ.ﺇ1,860 per night

Guest favorite

Home in East Hampton

4.94 out of 5 average rating, 202 reviews

Private beach Historical House with large property

Feb 8 – 15

ﺩ.ﺇ3,005 per night

Guest favorite

Home in Sag Harbor

4.92 out of 5 average rating, 122 reviews

Harbor Beach Cottage

Jul 13 – 20

ﺩ.ﺇ1,477 per night

Guest favorite

Guesthouse in Hampton Bays

4.96 out of 5 average rating, 146 reviews

WELCOME TO THE LOVE SHACK BY THE SEA

May 3 – 10

ﺩ.ﺇ1,304 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

Oct 5 – 12

ﺩ.ﺇ3,607 per night

Guest favorite

Guest suite in Hampton Bays

4.98 out of 5 average rating, 315 reviews

CHARMING OCEAN BUNGALOW

Oct 27 – Nov 3

ﺩ.ﺇ1,052 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 8 – 15

ﺩ.ﺇ1,135 per night

Guest favorite

Cottage in Southampton

4.96 out of 5 average rating, 100 reviews

Charming Southampton Light filled Cottage

Aug 13 – 20

ﺩ.ﺇ3,543 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

Jan 7 – 14

ﺩ.ﺇ2,735 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

Oct 27 – Nov 3

ﺩ.ﺇ1,043 per night

Superhost

Cottage in Laurel

4.75 out of 5 average rating, 274 reviews

North Fork Cottage

Dec 8 – 15

ﺩ.ﺇ647 per night

Guest favorite

Cottage in Montauk

4.91 out of 5 average rating, 516 reviews

Montauk Oceanview

Oct 9 – 16

ﺩ.ﺇ1,472 per night

Guest favorite

Cottage in Montauk

4.87 out of 5 average rating, 217 reviews

Waterfront Cottage, Fort Pond MTK

Jan 21 – 28

ﺩ.ﺇ3,359 per night

Superhost

Cottage in Cutchogue

4.69 out of 5 average rating, 187 reviews

Lovely 2 BR Beach House No. Shore

Apr 14 – 21

ﺩ.ﺇ725 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.

Nov 18 – 25

ﺩ.ﺇ1,044 per night

Guest favorite

Cottage in Montauk

4.91 out of 5 average rating, 139 reviews

Montauk Cottage Escape

Feb 14 – 21

ﺩ.ﺇ1,479 per night

Superhost

Cottage in New Suffolk

4.85 out of 5 average rating, 52 reviews

Mermaid cottage

May 6 – 13

ﺩ.ﺇ637 per night

Guest favorite

Cottage in Sag Harbor

4.98 out of 5 average rating, 49 reviews

Charming Scandinavian Inspired Beach Cottage

Aug 19 – 26

ﺩ.ﺇ3,787 per night

Guest favorite

Cottage in New Suffolk

4.94 out of 5 average rating, 48 reviews

Beach Cottage 3 - New Suffolk | NY

Sep 17 – 24

ﺩ.ﺇ1,074 per night

Guest favorite

Cottage in Mattituck

4.94 out of 5 average rating, 32 reviews

Cozy Cottage By The Bay, Farms & Vineyards!

Oct 6 – 13

ﺩ.ﺇ1,101 per night

Guest favorite

Cottage in Sag Harbor

4.95 out of 5 average rating, 86 reviews

Cozy Cottage by the Sea Sag Harbor

Jan 2 – 9

ﺩ.ﺇ3,364 per night

Guest favorite

Cottage in Hampton Bays

4.95 out of 5 average rating, 37 reviews

Hamptons Cottage.

Jul 14 – 21

ﺩ.ﺇ1,338 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
ﺩ.ﺇ331 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 200 homes with wifi, over 120 homes with a bbq area, 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

Home in Southampton

Home in East Hampton

Apartment in Sag Harbor

Home in East Hampton

Home in Sag Harbor

Guesthouse in Hampton Bays

Home in Sag Harbor

Guest suite in Hampton Bays

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 Montauk

Cottage in Cutchogue

Beach cottage rentals in Sag Harbor

Cottage in Southold

Cottage in Montauk

Cottage in New Suffolk

Cottage in Sag Harbor

Cottage in New Suffolk

Cottage in Mattituck

Cottage in Sag Harbor

Cottage in Hampton Bays

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