Hampton Bays holiday rentals

We found 2,499 holiday rentals — enter your dates for availability
Select from 304 homes, 27 cottages and other holiday rentals in Hampton Bays to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, such as parking and air conditioning. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Hampton Bays

Showing deals for:11 Dec - 18 Dec

Pool
Dining
Exterior
Pool
Exceptional
(6 reviews)

Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway

Hampton Bays

8% off
S$13,312
for 7 nights, 1 home
S$1,902 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway
Main Entrance
Dining table and picnic table
water view
Chef kitchen with breakfast area on 2nd floor
Heated pool with gorgeous water and natural wetland view
Exceptional
(37 reviews)

Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!

Southampton

8% off
S$11,204
for 7 nights, 1 home
S$1,601 per night
includes taxes & fees
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Dining Room
Private kitchen
Patio
Exterior
Exceptional
(100 reviews)

Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town

Sag Harbor

16% off
S$10,976
for 7 nights, 1 home
S$1,568 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
kitchen with large island and breakfast table
aerial view
view from living room towards pool, outdoor dining
master bedroom with balcony
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
S$74,121
for 7 nights, 1 home
S$10,589 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Living area
Terrace/patio
Living area
Exterior
Excellent
(10 reviews)

Stunning fall sunsets, coveted location on Mecox Bay - recently furnished

Water Mill

8% off
S$50,082
for 7 nights, 1 home
S$7,155 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Living area
Exterior
Interior
Pool
Exceptional
(36 reviews)

40-Foot Pool Retreat Near the Hamptons — Easy NYC Access, Total Relaxation

Center Moriches

12% off
S$5,083
for 7 nights, 1 home
S$726 per night
includes taxes & fees
40-Foot Pool Retreat Near the Hamptons — Easy NYC Access, Total Relaxation
Pool
Dining
living room
kitchen
Exceptional
(60 reviews)

Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool

Southampton

8% off
S$18,535
for 7 nights, 1 home
S$2,648 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
More vineyard views
Outdoor dining
Welcome to Vineyard View
Exterior
Exceptional
(26 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
S$9,304
for 7 nights, 1 home
S$1,329 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Interior
Exterior
Private kitchen
Outdoor dining
Exceptional
(8 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off
S$6,573
for 7 nights, 1 home
S$939 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Spacious Main Floor Living room
Exterior
Large Dining/Kitchen Space
Exterior
Exceptional
(11 reviews)

New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

Southold

7% off
S$11,346
for 7 nights, 1 home
S$1,621 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining  +10,)
Living area
park-like grounds
Front entrance, park-like grounds
Exceptional
(26 reviews)

Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool

Southampton

28% off
S$13,235
for 7 nights, 1 home
S$1,891 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Interior
Exterior detail
Living area
Interior
Exceptional
(14 reviews)

Farm and Wine Lovers’ Cottage Near the Hamptons

East Moriches

7% off
S$4,600
for 7 nights, 1 home
S$657 per night
includes taxes & fees
Farm and Wine Lovers’ Cottage Near the Hamptons
Private kitchen
.
Interior
3 acres of beautiful land
Exceptional
(81 reviews)

Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Hampton Bays

7% off
S$9,836
for 7 nights, 1 home
S$1,405 per night
includes taxes & fees
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Hot tub open all year
Exterior
Pool, gazebo, fire table
Living area
Exceptional
(44 reviews)

Westhampton Beach Town and Country

Westhampton Beach

8% off
S$10,315
for 7 nights, 1 home
S$1,474 per night
includes taxes & fees
Westhampton Beach Town and Country
Outdoor dining
Living area
Pool
Interior
Exceptional
(14 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

8% off
S$9,646
for 7 nights, 1 home
S$1,378 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Interior
Living area
Pool
Exceptional
(10 reviews)

Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house

Sag Harbor

8% off
S$13,373
for 7 nights, 1 cottage
S$1,910 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Room
Property grounds
Interior
Living area
Exceptional
(17 reviews)

Charming Riverhead home with large outdoor patio & backyard firepit

Riverhead

11% off
S$3,835
for 7 nights, 1 home
S$548 per night
includes taxes & fees
Charming Riverhead home with large outdoor patio & backyard firepit
Room
Living area
Grill + outdoor dining / furniture to dine al fresco!
Interior
Exceptional
(42 reviews)

Family and dog-friendly getaway near amazing wineries, beaches and restaurants!

Southold

7% off
S$7,913
for 7 nights, 1 home
S$1,130 per night
includes taxes & fees
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
This area is perfect for reading and relaxing
Kitchen is stocked with a selection of pots dishes and utensils
Spacious living room with sliders to the patio pool and backyard
Plenty of comfortable chairs for lounging
Exceptional
(108 reviews)

Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach

Westhampton Beach

7% off
S$6,025
for 7 nights, 1 home
S$861 per night
includes taxes & fees
Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach
75 inch TV w/ Bose Soundbar
Dining
Interior
Resort inspired backyard with heated pool, outdoor seating, and complete privacy
Exceptional
(16 reviews)

NEW DECK! Private 1 Acre Family Friendly Home - Heated Pool, Home Office & Gym

Westhampton

7% off
S$8,529
for 7 nights, 1 home
S$1,218 per night
includes taxes & fees
NEW DECK! Private 1 Acre Family Friendly Home - Heated Pool, Home Office & Gym
Stairs to the upstairs living room, kitchen and dining room
Pool
Large wrap-around lawn
Living room
Exceptional
(27 reviews)

Modern Family Retreat with Heated Pool, Playground and Peloton

Hampton Bays

8% off
S$10,435
for 7 nights, 1 home
S$1,491 per night
includes taxes & fees
Modern Family Retreat with Heated Pool, Playground and Peloton
Living area
Outdoor dining
Private kitchen
Pool
Exceptional
(13 reviews)

Explore the Hampton in this Shelter Island Getaway. Weekly Bookings

Shelter Island Heights

31% off
S$7,564
for 7 nights, 1 home
S$1,081 per night
includes taxes & fees
Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
Living area on 1st floor with wood burning fireplace
Featured as one of most beautiful poolsides
Couches on covered porch and outdoor dining table for 8
Kitchen walks out to covered porch across length of entire back
Exceptional
(7 reviews)

IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES

Southampton

8% off
S$23,942
for 7 nights, 1 home
S$3,420 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
Dining
Pool
Interior
Exterior
Wonderful
(20 reviews)

2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub

Riverhead

7% off
S$5,634
for 7 nights, 1 home
S$805 per night
includes taxes & fees
2-Acre Modern Estate in Southampton. Beach, winery, farm, pool, and hot tub
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The beachside setting of Hampton Bays is ready to explore

The beaches and wildlife provide a pleasant backdrop to your holiday home in Hampton Bays. This city's boating, windsurfing and canoeing draw many visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in Hampton Bays

Are you searching for attractions to visit during your stay? Venture out of your holiday home and experience everything that makes Hampton Bays a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Shinnecock Hills Golf Course (4.4 mi / 7.1 km)
  • Jamesport Vineyards (6.9 mi / 11.1 km)
  • Paumanok Vineyards (7.1 mi / 11.5 km)
  • Duck Walk Vineyards (8.2 mi / 13.2 km)
  • Macari Vineyards (8.5 mi / 13.7 km)
  • Martha Clara Vineyards (8.7 mi / 14 km)

Exploring the natural landscape of Hampton Bays

Whether you're an active traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Hampton Bays. These are some of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Meschutt Beach (2 mi / 3.2 km)
  • Ponquogue Beach (2.6 mi / 4.1 km)
  • Shinnecock East County Park (3 mi / 4.8 km)
  • Cooper's Beach (5.9 mi / 9.4 km)
  • The Hamptons Beaches (11.9 mi / 19.2 km)
  • Havens Beach (15.2 mi / 24.5 km)

Seasonal weather averages in Hampton Bays

If you're planning a holiday around the weather, August, July, September and June are the hottest months to visit, when temperatures average 21°C.

Travelling to and around Hampton Bays

The nearest airport is in Westhampton, NY (FOK-Francis S. Gabreski), located 6.7 mi (10.8 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into East Hampton, NY (HTO), which is 15.5 mi (24.9 km) away.

If you prefer train travel, you can make your way to Hampton Bays Station.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Hampton Bays?
Based on our data, houses are the most in-demand type of property in Hampton Bays. But as you know, everyone's idea of the perfect trip differs. Vrbo has holiday rentals of all sizes and shapes, so you're bound to find the perfect fit.
How much does it cost to rent a holiday rental in Hampton Bays?
The average price for a holiday rental in Hampton Bays is determined by several factors, including length of stay, season and property type. Whether you'd like a sprawling villa with a pool or a comfy cabin for just you and the kids, just enter your travel dates to view stays with fantastic value.
How much does it cost to rent a beach house in Hampton Bays?
When you travel and the style and size of the property will help determine the cost of your beachside escape. Type in your Hampton Bays travel dates to view your available options on Vrbo. Can't live without a private pool? Use our filters to choose the features and amenities you want.
What are popular rental amenities in Hampton Bays?
When it comes to rental amenities that guests look for in Hampton Bays, a chef, a swimming pool and a nearby waterfront rank the highest. With Vrbo holiday homes, you'll have options to suit your taste and style, whether you're on a trip with family, friends or even pets.
What are the top attractions for families in Hampton Bays?
Keep the kids happy at these popular family-friendly attractions in Hampton Bays:
  • Coopers Beach
  • The Hamptons Beaches
  • Long Island Aquarium and Exhibition Centre
Can I find two-bedroom holiday rentals in Hampton Bays?
You can select from 23 two-bedroom holiday homes in Hampton Bays. Give the kids the second room or maybe fill it with a couple of your besties. There's space for whoever's fortunate enough to be joining your journey.
Are there holiday rentals with WiFi in Hampton Bays?
Whether you'd like to stay in touch with world events, reply to emails or post a pic to social media, there are 95 holiday homes with WiFi in Hampton Bays. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.
How old do you have to be to rent a holiday rental in Hampton Bays?
The minimum age requirements can differ between properties on Vrbo, so double-check the rules of the holiday home in Hampton Bays you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Hampton Bays for?
How long you can book a holiday rental in Hampton Bays is down to the property. Just enter your preferred dates to see a list of options offering extended stays. With lots of features like full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to find a perfect place to call your home away from home in Hampton Bays.

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