Bridgehampton Holiday Rentals

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Holiday Rentals in Bridgehampton

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (15)
"Tucked away in a quiet residential area. Rooms were clean and kitchenette was well equipped. Private parking spot in the driveway next to the cottage was a bonus. Highly recommended!"
The price is AU$628
includes taxes & fees
1 Oct - 2 Oct
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (74)
"We had an AMAZING stay at Eunyoung and Mark's magical cottage. The property was exactly as described. Eunyoung and Mark are delightful people. Tranquil, quiet, peaceful. "
Fairy Tale Guest Cottage in Magic Garden by Pool

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (295)
"Very nice & affordable "
The price is AU$263
includes taxes & fees
19 Oct - 20 Oct
Windward Shores Ocean Resort

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (414)
"We loved it, suite size was great! "
The price is AU$254
includes taxes & fees
20 Oct - 21 Oct
Montauk Oceanside Suites

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (240)
"Great view of the water and nice amenities with the beach and pool."
The price is AU$521
includes taxes & fees
5 Oct - 6 Oct
Cliffside Resort Condominiums

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (232)
"Great place to stay for small family "
The price is AU$322
includes taxes & fees
30 Sept - 1 Oct
Driftwood Resort

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.8 out of 10, Excellent, (28)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

9.8 out of 10, Exceptional, (32)
"Our trip was amazing, the pool was in perfect condition and the house had everything we needed. Would definitely stay here again!!"
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

9.8 out of 10, Exceptional, (96)
"Very Nice stay there for business would go back for pleasure"
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

9.6 out of 10, Exceptional, (136)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

MONTAUK MANOR-DELUXE STUDIO APARTMENT

9.8 out of 10, Exceptional, (74)
"The room was very nicely decorated and clean and had everything you would need. We enjoyed our stay here and appreciated not having to bring linens and towels to a vrbo rental. The only issues we faced not booking directly with the hotel was not being able to use hotel shuttle to town and we ran out of toilet paper and the front desk said they are not supoosed to provide it as we didnt book through them. Other than that the property is very nice providing seating outside to enjoy a beautiful...
MONTAUK MANOR-DELUXE STUDIO APARTMENT

Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

9.8 out of 10, Exceptional, (53)
"Our family (16) spent a week at the property and found the house and property in good order, comfortable and convenient to the bay and other attractions. I would definitely recommend it as a great family vacation."
Mansion Near the Bay. 7 bedrooms! Chef’s kitchen.

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (99)
"My husband and I brought our puppy. He had a great time running around the yard and beach. We enjoyed our stay and hope to return. The property is beautiful and we were very happy to find a pet friendly place on the water and close to town."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

10.0 out of 10, Exceptional, (105)
"Very walkable charming stay in beautiful area that supports larger group. Carter is very responsive and friendly. "
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (95)
"We loved our stay - it was nice to be a short walk away from the bay and the pool was great. The home was very clean and comfortable."
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

10.0 out of 10, Exceptional, (190)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
The price is AU$1,361
includes taxes & fees
2 Oct - 3 Oct
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

10.0 out of 10, Exceptional, (88)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Charming Montauk Getaway centrally located

9.8 out of 10, Exceptional, (55)
"The property was well located and the host had provided for amenities like beach chairs and towels. The property had a private fenced in yard with amenities. "
Charming Montauk Getaway centrally located

10 Bedroom Hampton House with a regulation size Pickleball court

10.0 out of 10, Exceptional, (32)
"Cannot say enough good things. Unique, sprawling, beautiful property with more than enough room for a large group. Endless entertainment, great pool, walking distance from a few bars and restaurants. Great communication and accommodation from our host. Would recommend and rent again."
10 Bedroom Hampton House with a regulation size Pickleball court

Charming Sag Harbor Retreat with Private Pool, Minutes to Beaches and Town

Charming Sag Harbor Retreat with Private Pool, Minutes to Beaches and Town
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bridgehampton Hotel Reviews

Find out more about Bridgehampton

Find out more about Bridgehampton

Everything you need to know about Bridgehampton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Bridgehampton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bridgehampton holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Bridgehampton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bridgehampton. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bridgehampton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bridgehampton holiday rentals we have selected for you start as low as AU$254 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Bridgehampton rentals

At Expedia, we put the best Bridgehampton holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Bridgehampton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bridgehampton holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bridgehampton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Bridgehampton?

Yes, there are holiday rentals in Bridgehampton close to South Fork Natural History Museum and Nature Center, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Bridgehampton speak positively about the beaches and restaurants in this destination. Make sure you have time to check out the wineries and gardens during your trip.

What are some of the best holiday rentals that Bridgehampton has to offer?

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor : This highly rated holiday home rental in Bridgehampton offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a patio, a garden and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Bridgehampton?

Choose from 84 Expedia holiday rentals in Bridgehampton for a memorable holiday.

What can I see and do in Bridgehampton?

Family-friendly attractions include South Fork Natural History Museum and Nature Center and Children's Museum of The East End, whereas The Hamptons Beaches and Ocean Road Beach are a couple of great spots to enjoy the outdoors. While here, Channing Daughters Winery and Mecox Bay are other places worth a visit.

What are holiday rentals like in Bridgehampton?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bridgehampton. Holiday rentals feature extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.