Holiday rentals in Bridgehampton

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Top-rated holiday rentals in Bridgehampton

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Flat in Sag Harbor
4.92 out of 5 average rating, 173 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".)

Guest favourite
A sparkling heated pool is framed by wooden decking, surrounded by lush greenery. Sunlight reflects off the clear blue water, creating a refreshing atmosphere. Lounge chairs are positioned nearby, offering a comfortable space for relaxation.
Home in Bridgehampton
4.77 out of 5 average rating, 52 reviews

Cheerful 3 bedrm-4 beds-3 bath -beach home w pool

Heart of the Hamptons is situated this bright, beach house 5 min from the ocean, BH/Sag Harbor town, & Wolfer vineyards. 2 master suites w/ ensuite bathrooms and an additional guest room with adjacent bathroom that comfortably sleeps 6 -1 King, 1 queen, 2 twin. Open kitchen that adjoins the dining area and the double height living room w/ fireplace. Sparkling heated (add charge) pool (MD-mid Sept) and palatial lawns with room to roam. Keep it simple at this peaceful and centrally located getaway

Top guest favourite
A spacious bedroom is featured with a comfortable king-sized bed, adorned with soft linen and decorative pillows. Nightstands with stylish lamps provide gentle illumination, complementing the calm color scheme of the room.
Flat in Bridgehampton
4.96 out of 5 average rating, 82 reviews

Hamptons Elegant and Comfortable Apartment

Enjoy your stay in this beautifully decorated and completely private basement apartment - with all original artwork- in the center of the Hamptons with the added convenience of being close to major towns and beaches. Large bedroom with comfortable king sized bed and high quality mattress and linen. Large-screen smart TV with many channels. Closet space, well equipped kitchenette, bathroom with glass-enclosed shower. Seating area for 4 and second large-screen smart-TV with comfy oversized couch.

Guest favourite
Flat in Southampton
5 out of 5 average rating, 26 reviews

Southampton apt walk to village

Enjoy easy access to everything from this perfectly located Apt in Southampton Village . 10 minutes walk to downtown restaurants, bars and shopping 1.5 miles to our Glorious Village Beaches. located in a diverse, local Southampton Village neighborhood, centrally located to all Hamptons, Sag Harbor and Montauk & the North fork This place is perfect for a natural lover our garden is a pollinator sanctuary home to birds ,🐝 , 🦋 , and other creatures . We love pets so your furry baby is welcome

Guest favourite
An inviting living area features a cozy seating arrangement with a light-colored sofa and accent chairs. A wood-burning fireplace is surrounded by a stone mantle, while natural light fills the space through large windows. A dining area, art pieces, and wooden beams complement the bright atmosphere.
Cottage in Bridgehampton
4.95 out of 5 average rating, 109 reviews

Calf Creek Cottage (Water Mill/Bridgehampton)

Enjoy the peaceful seclusion of this charming, updated 3 bedroom, 2 bath cottage located on a private, acre-sized flag-lot south of the highway right on the border of Water Mill and Bridgehampton. Each bedroom (1 king, 2 queen) features ample closet space and new smart TVs . The new, fully-stocked kitchen, propane BBQ, outdoor dining table for 8, outdoor shower and spa with lounge furniture, and wood burning fireplace make it the perfect getaway for either summer or the winter season. Pets OK.

Guest favourite
The exterior of a spacious two-story house is highlighted, surrounded by lush greenery. A clear saltwater pool features a light blue hue, with several lounge chairs positioned along the patio. Large windows adorn the house, inviting natural light into the interior.
Home in Sag Harbor
5 out of 5 average rating, 7 reviews

Designer home in Sag Harbor : 5BR walk to beach

Nestled in Sag Harbor, this elegant 5-bedroom home offers a saltwater heated pool just 2 miles away from the town. A mere five-minute stroll takes you to the Serene Green local farm stand and Long Beach Bay, where you can indulge in swimming, paddleboarding, and witnessing breathtaking sunsets. The chef's kitchen is perfect for culinary adventures, and you can savor your meals either poolside under the charming string lights at the 8-person farm table or indoors at the 8-person table

Top guest favourite
An inviting outdoor sitting area features wooden chairs positioned near French doors. The space is surrounded by lush greenery, and a stone pathway leads to the entrance of the studio apartment. Flowering vines and potted plants add a touch of nature.
Guest suite in Sag Harbor
4.9 out of 5 average rating, 397 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. Fully self contained and private. Main Street is lively and all restaurants are open. Central heat with it’s own thermostat controls & AC. Working fireplace and spacious bathtub make for an ideal cozy and romantic getaway. Parking in driveway close to entrance. Not suitable for infants or children.

Top guest favourite
Flat in Sag Harbor
4.94 out of 5 average rating, 144 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 .

Guest favourite
A light-filled living area features a comfortable sectional sofa with decorative pillows. A coffee table rests on a textured area rug, accompanied by framed art on the white walls. Natural light enters through a window overlooking greenery, accentuating a serene environment.
Flat in Southampton
4.89 out of 5 average rating, 57 reviews

Spacious One Bedroom Apt, Close to Beaches

1 bedroom basement apartment with full size windows, king bed, double sink vanity, walk in closet, full kitchen, private entrance, and close proximity to town and beaches. Parking on premises, access to washer/dryer for long term guests. Centrally located between Southampton and Sag Harbor. Air mattress must be requested. Full size crib, pack n play, bassinet, high chair must be requested. 1.5 miles to the bay beaches 5 miles to closest ocean beaches

Top guest favourite
Guest house in Southampton
4.96 out of 5 average rating, 463 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate cottage is the perfect getaway! Nestled in an 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 or to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, golf, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet.

Guest favourite
Home in Sag Harbor
4.95 out of 5 average rating, 317 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.

Guest favourite
A well-appointed seating area is situated beside a sparkling blue pool, featuring a beige lounge sofa and matching chairs. An oversized turquoise umbrella provides shade, while the surrounding greenery enhances the outdoor ambiance. A white house is visible in the background.
Loft in Southampton
4.88 out of 5 average rating, 107 reviews

Oasis Hampton getaway

Located in the heart of southampton. 3miles away from main shopping areas.Room is newly remodeled and furnished . All upscale Ammenities. Electric toilet ,free WiFi, free Netflix , use of pool and bbq grill, fire pit, living room with 52”flat screen tv, kitchenette and dining area and driveway parking .

Popular amenities for Bridgehampton holiday rentals

When is the best time to visit Bridgehampton?

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Avg. price£820£891£889£792£883£972£1,119£1,224£816£809£750£820
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Bridgehampton?

    Bridgehampton has more than 250 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Bridgehampton?

    Experience the best of Bridgehampton with our house rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Bridgehampton?

    Four-legged friends are welcome in Bridgehampton. Choose from more than 150 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Bridgehampton?

    Yes! Work meets play with ease at over 160 vacation rentals in Bridgehampton featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Bridgehampton vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 240 vacation homes with pools in Bridgehampton, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Bridgehampton?

    Make yourself at home in Bridgehampton by choosing from our most frequently booked neighborhoods. We have over 840 vacation rentals in Sagaponack, over 1,980 vacation rentals in Bridgehampton, and over 1,980 vacation rentals in Water Mill.

  • Do house rentals in Bridgehampton have air conditioning?

    Absolutely! We offer over 230 house rentals with air conditioning in Bridgehampton. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Bridgehampton have a kitchen?

    Absolutely! We offer over 10 cottage rentals with a kitchen in Bridgehampton. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Bridgehampton have wifi?

    Absolutely! We offer over 10 cottage rentals with wifi in Bridgehampton. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Bridgehampton have free parking?

    Absolutely! We offer over 10 cottage rentals with free parking in Bridgehampton. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Bridgehampton

  • Total holiday rentals

    Explore 280 holiday rentals in Bridgehampton

  • Nightly prices starting at

    Bridgehampton holiday rentals start at £104 per night before taxes and fees

  • Verified guest reviews

    Over 3,080 verified reviews to help you choose

  • Family-friendly holiday rentals

    250 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 150 rentals that welcome pets

  • Holiday rentals with a pool

    240 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wifi availability

    280 of Bridgehampton holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Bridgehampton rentals

  • 4.8 Average rating

    Bridgehampton stays are highly rated by guests – averaging 4.8 out of 5!

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