Book Holiday Homes in Hampton Bays

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Featured Holiday Homes in Hampton Bays

Enjoy Autumn with us.

Enjoy Autumn with us.

Southold
Located in Southold, this vacation home is by the sea, within a 5-minute drive of The Old Field Vineyards and Sparkling Pointe.
Enjoy Autumn with us.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Eastport
Located in Eastport, this vacation home is near the beach, a 3-minute walk from Moriches Bay and within a 5-minute drive of Long Island Skydiving Center.
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms
Beautiful Private 4 BR, Heated Pool. Close to Everything.

Beautiful Private 4 BR, Heated Pool. Close to Everything.

East Hampton
With a stay at this vacation home in East Hampton, you'll be near the beach, within a 10-minute drive of The Hamptons Beaches and Three Mile Harbor.
Beautiful Private 4 BR, Heated Pool. Close to Everything.
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Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub

Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub

Westhampton
With a stay at this vacation home in Westhampton, you'll be on the waterfront, within a 10-minute drive of The Hamptons Beaches and Westhampton Beach Performing ...
Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub
Village Fringe Available May 24th - October 31st. Family/Pet Friendly

Village Fringe Available May 24th - October 31st. Family/Pet Friendly

East Hampton
With a stay at this vacation home in East Hampton (East Hampton North), you'll be within a 5-minute drive of The Hamptons Beaches and East Hampton Historical ...
Village Fringe Available May 24th - October 31st. Family/Pet Friendly
Mastic Beach Surf House

Mastic Beach Surf House

Mastic Beach
Located in Mastic Beach, this vacation home is on the waterfront, a 3-minute drive from William Floyd Estate and 7 minutes from Carmans River.
Mastic Beach Surf House
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr

Westhampton Beach
With a stay at this vacation home in Westhampton Beach, you'll be by the sea, within a 5-minute drive of The Hamptons Beaches and Westhampton Beach Performing ...
WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

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

Southampton
With a stay at this vacation home in Southampton, you'll be within a 10-minute drive of The Hamptons Beaches and Southampton Golf Range.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

East Hampton
With a stay at this vacation home, you'll be centrally located in East Hampton, within a 5-minute drive of The Hamptons Beaches and Three Mile Harbor.
Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
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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.

Hampton Bays Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Hampton Bays vacation homes are the perfect way for you to wing it.

Holiday houses in Hampton Bays let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Hampton Bays in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Hampton Bays adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Hampton Bays with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Hampton Bays vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Hampton Bays Holiday Homes essential information

Accommodation
1367 Holiday Homes
Lowest Price
AU$267
Highest Price
AU$752
Popular accommodation
Enjoy Autumn with us., 11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms, Beautiful Private 4 BR, Heated Pool. Close to Everything., Family Friendly 6 Bedroom Waterfront 3 Acre Pool & Hot Tub , Village Fringe Available May 24th - October 31st. Family/Pet Friendly, Mastic Beach Surf House, WHB Village,4200sqft,Traffic Free,Private Drive,40ft Heated Pool,Beach,Family Fr, Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping, Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

Top trending hotels in Hampton Bays

10 Bedroom Hampton House with a regulation size Pickleball

10 Bedroom Hampton House with a regulation size Pickleball

Hampton Bays
With a stay at this vacation home in Hampton Bays, you'll be near the beach, within a 5-minute drive of The Hamptons Beaches and Ponquogue Beach.
10 Bedroom Hampton House with a regulation size Pickleball
Canoe Place Inn and Cottages

Canoe Place Inn and Cottages

4 out of 5
239 E Montauk Hwy, Hampton Bays, NY
The price is AU$752 per night from 6 Mar to 7 Mar
AU$752
includes taxes & fees
6 Mar - 7 Mar
With a stay at Canoe Place Inn and Cottages in Hampton Bays, you'll be near the beach, within a 5-minute drive of The Hamptons Beaches and Meschutt Beach.
Canoe Place Inn and Cottages
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

2 out of 5
2 W Montauk Hwy, Hampton Bays, NY
The price is AU$267 per night from 28 Feb to 1 Mar
AU$267
includes taxes & fees
28 Feb - 1 Mar
With a stay at Hampton Bays Hotel on Main in Hampton Bays, you'll be a 3-minute drive from The Hamptons Beaches and 6 minutes from Meschutt Beach.
Hampton Bays Hotel on Main
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Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

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

Hampton Bays
With a stay at this vacation home in Hampton Bays, you'll be on the beach, within a 5-minute drive of The Hamptons Beaches and Meschutt Beach.
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!
Don't see what you're looking for?
See all available properties in Hampton Bays
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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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^Subject to availability and chosen travel dates.