Hampton Bays holiday rentals

We found 2,497 holiday rentals — enter your dates for availability
Select from 303 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:25 Dec - 1 Jan

Chef kitchen with breakfast area on 2nd floor
Dining table and picnic table
water view
Main Entrance
2nd floor deck with additional dining and leisure seating.
Exceptional
(38 reviews)

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

Southampton

5% off
S$18,631
for 7 nights, 1 home
S$2,662 per night
includes taxes & fees
Luxurious Waterfront Retreat in Southampton: Breathtaking Views, Pool, and More!
Pool
Dining
Exterior
Pool
Exceptional
(6 reviews)

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

Hampton Bays

8% off
S$13,358
for 7 nights, 1 home
S$1,908 per night
includes taxes & fees
Newly Built Hamptons House, Pool, Beach Access + Easy Access off Montauk Highway
The Harbor
Private kitchen
Exterior
Dining Room
Exceptional
(103 reviews)

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

Sag Harbor

16% off
S$10,814
for 7 nights, 1 home
S$1,545 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
master bedroom with balcony
aerial view
view from living room towards pool, outdoor dining
kitchen with large island and breakfast table
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
S$74,790
for 7 nights, 1 home
S$10,684 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Living area
Terrace/patio
Pool
Exterior
Excellent
(10 reviews)

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

Water Mill

8% off
S$50,534
for 7 nights, 1 home
S$7,219 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Dining
Living area
Children’s area
Private kitchen
Exceptional
(15 reviews)

Beautiful Hamptons Family Escape.

Westhampton

8% off
S$9,222
for 7 nights, 1 home
S$1,317 per night
includes taxes & fees
Beautiful Hamptons Family Escape.
Dining Room with seating for Ten
Pool
Exterior
Outdoor dining
Exceptional
(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
S$11,099
for 7 nights, 1 home
S$1,586 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Large Dining/Kitchen Space
Exterior
Pool
Exterior
Exceptional
(11 reviews)

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

Southold

8% off
S$16,439
for 7 nights, 1 home
S$2,348 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Interior
Exterior
Outdoor dining
Private kitchen
Exceptional
(8 reviews)

Beautiful Colonial Mint Condition Summer House Walking Distance to Beach

Jamesport

12% off
S$5,645
for 7 nights, 1 home
S$806 per night
includes taxes & fees
Beautiful Colonial Mint Condition Summer House Walking Distance to Beach
Living area
Outdoor dining
Welcome to Vineyard View
More vineyard views
Exceptional
(26 reviews)

Vineyard View, Bike to the Most Beautiful Beach

Mattituck

8% off
S$9,090
for 7 nights, 1 home
S$1,299 per night
includes taxes & fees
Vineyard View, Bike to the Most Beautiful Beach
Pool
Dining
living room
outdoor shower
Exceptional
(60 reviews)

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

Southampton

7% off
S$18,778
for 7 nights, 1 home
S$2,683 per night
includes taxes & fees
Southampton Village Renovated Sun-filled Charming Home, Heated Salt water Pool
Lower deck With Pool, 9 Loungers, plus 6 pool-chairs. Upper deck dining seats 10
Living area
Front entrance, park-like grounds
An elegant dining room (to 10 ppl, joins kitchen +8 and outdoor dining  +10,)
Exceptional
(26 reviews)

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

Southampton

28% off
S$13,428
for 7 nights, 1 home
S$1,918 per night
includes taxes & fees
Southampton Pickleball Walk to beach. Kayaks on lake Park-like grounds Pool
Spacious living room with sliders to the patio pool and backyard
Kitchen is stocked with a selection of pots dishes and utensils
Plenty of comfortable chairs for lounging
Enjoy nearby North Fork and South Fork wineries and many other local attractions
Exceptional
(108 reviews)

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

Westhampton Beach

7% off
S$8,304
for 7 nights, 1 home
S$1,186 per night
includes taxes & fees
Hampton’s Haven: Heated Pool, Hot Tub & Gameroom! 2 miles to Rogers Beach
Interior
Living area
Outdoor dining
Living area
Exceptional
(15 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

7% off
S$9,969
for 7 nights, 1 home
S$1,424 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Pool
Living area
Interior
Exterior detail
Exceptional
(11 reviews)

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

Sag Harbor

8% off
S$13,191
for 7 nights, 1 cottage
S$1,884 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Private kitchen
.
3 acres of beautiful land
Outdoor dining
Exceptional
(82 reviews)

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

Hampton Bays

6% off
S$10,814
for 7 nights, 1 home
S$1,545 per night
includes taxes & fees
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14
Dining area
Exterior
Living area
Pool, gazebo, fire table
Exceptional
(45 reviews)

Westhampton Beach Town and Country

Westhampton Beach

8% off
S$10,487
for 7 nights, 1 home
S$1,498 per night
includes taxes & fees
Westhampton Beach Town and Country
Interior
Exterior detail
Private kitchen
Living area
Exceptional
(15 reviews)

Farm and Wine Lovers’ Cottage Near the Hamptons

East Moriches

7% off
S$5,125
for 7 nights, 1 home
S$732 per night
includes taxes & fees
Farm and Wine Lovers’ Cottage Near the Hamptons
Outdoor dining
Dining
Living area
Room
Exceptional
(18 reviews)

Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe

Cutchogue

8% off
S$6,555
for 7 nights, 1 cottage
S$936 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Exterior
Property grounds
Interior
Room
Exceptional
(17 reviews)

Charming Riverhead home with large outdoor patio & backyard firepit

Riverhead

11% off
S$3,871
for 7 nights, 1 home
S$553 per night
includes taxes & fees
Charming Riverhead home with large outdoor patio & backyard firepit
Dining
Dining
Room
Exterior
Exceptional
(10 reviews)

Southampton Village Charmer - South of Highway

Southampton

8% off
S$29,222
for 7 nights, 1 home
S$4,175 per night
includes taxes & fees
Southampton Village Charmer - South of Highway
Open entry foyer with wall of windowed doors to Zen Garden
Thermador chefs kitchen with expansive island open to dining room & family room
Dining room seating 12 leading to chef's kitchen and doors leading to pool
Frankel Residence
Exceptional
(6 reviews)

Completely Renovated Home on ~2 Private Acres, Near Beach/Town

Wainscott

8% off
S$21,436
for 7 nights, 1 home
S$3,062 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Living Room
Pool
Private Yoga Room
Game Room w Home Theater System
Exceptional
(14 reviews)

Luxe Westhampton Beach Home w/ Pool & Hot Tub

Westhampton Beach

5% off
S$12,066
for 7 nights, 1 home
S$1,724 per night
includes taxes & fees
Luxe Westhampton Beach Home w/ Pool & Hot Tub
Couches on covered porch and outdoor dining table for 8
Featured as one of most beautiful poolsides
Kitchen walks out to covered porch across length of entire back
Hydrangeas blooming all summer.these are the August bloomers
Exceptional
(7 reviews)

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

Southampton

8% off
S$24,778
for 7 nights, 1 home
S$3,540 per night
includes taxes & fees
IN THE ViILLAGE OF SOUTHAMPTON POOL,TENNIS,PICKLEBALL COURTS BEACH CHAIRS&BIKES
  • 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)
  • Safari Adventure (9.1 mi / 14.7 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)
  • Tiana Beach (2.5 mi / 4.1 km)
  • Ponquogue Beach (2.6 mi / 4.1 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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