Bridgehampton Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Bridgehampton vacation rentals

Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (312 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is CA $218
CA $286 total
includes taxes & fees
May 14 - May 15
Windward Shores Ocean Resort
Apartment

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (426 reviews)
"Awesome room!!! Wish I could come back in the summer"
United States
Nicki
The price is CA $225
CA $272 total
includes taxes & fees
May 14 - May 15
Montauk Oceanside Suites
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is CA $276
CA $375 total
includes taxes & fees
May 31 - Jun 1
Cliffside Resort Condominiums
Flat-screen TV

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
"Great stay & great staff!"
United States
James
The price is CA $281
CA $321 total
includes taxes & fees
May 14 - May 15
North Fork Cottages & RV Resort
Property grounds

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (237 reviews)
"Wonderful location, right on the beach. The staff was kind and welcoming. The property was beautiful with a pool, playground, tennis and basketball courts, cornhole, etc. Very family friendly. Some walkable restaurants nearby and a quick 5-10 minute drive into town where a lot of the restaurants and shops are. We did have ants all in our food one day but the staff addressed it quickly "
United States
John
The price is CA $213
CA $288 total
includes taxes & fees
May 18 - May 19
Driftwood Resort
One Bedroom Condo King with Ocean view | Living area

Offshore Residences

Offshore Residences
4.5 star property
Downtown Montauk
10.0 out of 10, Exceptional, (1 review)
The price is CA $721
CA $980 total
includes taxes & fees
May 14 - May 15
Offshore Residences
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bridgehampton Hotel Reviews

Ocean Surf Resort

Ocean Surf Resort

2/10 Terrible
"We were very disappointed after we got home and saw our card was charged about $40. When I called I was told it was a hotel tax. When I book through Expedia I assume it’s a One stop shop to book trips and pay what I owe at time of booking, not have a surprise charge for something made up. You work hard to try and afford a trip and then get charged more money. Expedia contacted them to try and remedy and they said to agent, it was for WiFi, CHAIRS, TOWELS! What does that even mean?! We were there one night in May, no chairs were used or towels, we didn’t even use the shower! Needless to say, that was our last time at this place. BEWARE OF EXTRA weird charges."
Christina 1-night trip
Posted 10 hours ago
Ocean Surf Resort

Find out more about Bridgehampton

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Bridgehampton. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Bridgehampton?

Yes, there are vacation rentals in Bridgehampton close to Children's Museum of The East End, or you can go with a 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's the top vacation rental that Bridgehampton has to offer?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: This vacation home rental near Bridgehampton offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Bridgehampton?

Choose from 87 Expedia vacation rentals in Bridgehampton for a memorable vacation.

What can I see and do in Bridgehampton?

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

What are vacation rentals like in Bridgehampton?

Vacation rentals are private properties you can book for a couple of days or more in Bridgehampton. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for small groups.