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Eastport Holiday Rentals

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Holiday Rentals in Eastport

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (34)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

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

East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

10.0 out of 10, Exceptional, (102)
"Great indoor and outdoor spaces to hang out. Took SUP on the water - so nice and calm. "
The price is AU$798
includes taxes & fees
16 Oct - 17 Oct
East End Retreat - Water Front - Available for the US Open Shinnecock Hills 2026

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (20)
"Stay away"
The price is AU$423
includes taxes & fees
19 Oct - 20 Oct
Walk to Beach 2BR Near Dining & Shopping

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

Modern Vacation home. Close to The Hamptons

10.0 out of 10, Exceptional, (3)
"good time"
The price is AU$985
includes taxes & fees
14 Oct - 15 Oct
Modern Vacation home. Close to The Hamptons

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

9.6 out of 10, Exceptional, (137)
"Perfect property to hangout and stay entertained for hours"
Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!

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

10.0 out of 10, Exceptional, (191)
"Had a lovely relaxing time with family and friends. Very convenient and great size."
The price is AU$1,956
includes taxes & fees
17 Oct - 18 Oct
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

1856 Trading House w/ walk to water

9.6 out of 10, Exceptional, (50)
"The place was lovely and well appointed.. Beds were comfy. The spiral staircase was a bit tight to maneuver but location was perfect. It was a great spot for us, close to family in Sound Beach and Miller Place."
1856 Trading House w/ walk to water

Cozy Country Cottage #3

10.0 out of 10, Exceptional, (27)
"Very clean and comfortable "
The price is AU$501
includes taxes & fees
23 Oct - 24 Oct
Cozy Country Cottage #3

Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

2.0 star property
8.4 out of 10, Very good, (7)
"prefect experience! The house is clean and well decorated with a large organized yard. Many parking spaces. "
The price is AU$1,400
includes taxes & fees
17 Oct - 18 Oct
Spacious multiples bedroom house in enchanting Calverton with WiFi, AC

Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

9.6 out of 10, Exceptional, (23)
"This was the perfect location to enjoy the vineyards for my friend’s bachelorette party. Everyone had a comfy room and the space was very generous. Additionally the yard was massive and had ample seating. We had a great time and would definitely recommend this to all!"
Spacious home near Aquarium & heart of wine country Shopping & close to Hamptons

Stylish Five-Bedroom Oasis w/ Pool, Minutes from Beaches, Wineries & the...

10.0 out of 10, Exceptional, (1)
"the house is huge and well appointed. the outdoor space with the huge handsome awning set the stage. couch outside should be replaced but it's a small complaint in the big scheme of this house. updated bathrooms and bedrooms with four twin beds in total - very flexible living. pool outstanding, very deep and beautiful setting outside. could upgrade patio loungers but again not really detrimental and kind of charming"
Stylish Five-Bedroom Oasis w/ Pool, Minutes from Beaches, Wineries & the...

Tranquil Stay

10.0 out of 10, Exceptional, (6)
"Great stay with family to see a couple of our son's shows at the Gateway Theatre. Thank you Andre for be a great host...!!!"
The price is AU$860
includes taxes & fees
22 Oct - 23 Oct
Tranquil Stay

Beach, Pool, Wine, Shopping!

10.0 out of 10, Exceptional, (73)
"The check-in process and communication couldn't have been easier. The property was clean, comfortable, and had everything we needed to enjoy ourselves. Conveniently located a walkable distance from Love Lane and a short drive from wineries (which is what brought us to the area)"
Beach, Pool, Wine, Shopping!

Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

9.8 out of 10, Exceptional, (16)
"Had an amazing stay here and would definitely recommend to others!! Only issue was the heat did not work in certain areas. House and backyard / pool area was spacious and beautiful. Perfect for large groups. Would definitely stay again."
Quintessential Hamptons home with 6 bedrooms (all ensuite bathrooms), open...

Summer getaway

9.0 out of 10, Wonderful, (14)
"Perfect location for a family holiday "
Summer getaway

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

9.4 out of 10, Exceptional, (73)
"Enjoyed our time. Thank you "
Southampton Estate, Newly Renovated , Excellent For Families! Sleeps 12-14

Private beach on a fenced in property sunset views

10.0 out of 10, Exceptional, (12)
"We liked our stay there. Clean house, beautiful sunset as described. Close to the beach. Very nice stay."
Private beach on a fenced in property sunset views

Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

9.4 out of 10, Exceptional, (41)
"I went with family for a memorial celebration for a family member who had passed away. Worked out great and enjoyed the back deck & fire pit! Also, beds were comfy and open kitchen & LR were great for entertaining! Thank you Billy:)"
The price is AU$568
includes taxes & fees
15 Oct - 16 Oct
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!
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 Eastport Hotel Reviews

Find out more about Eastport

Find out more about Eastport

Everything you need to know about Eastport 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 Eastport 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 Eastport holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Eastport holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Eastport. 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 Eastport 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 Eastport holiday rentals we have selected for you start as low as AU$423 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Eastport rentals

At Expedia, we put the best Eastport 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 Eastport 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 Eastport 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 Eastport. 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 Eastport?

Yes, there are holiday rentals close to the most popular sights in Eastport, or you can select a more secluded option if you're looking for a relaxing stay. Eastport is known for its restaurants and wineries. Make sure you have time to check out the shopping while you're in the area.

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

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms: This highly rated holiday home rental in Eastport is located on the waterfront, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Eastport?

Choose from 9 Expedia holiday rentals in Eastport for a memorable holiday.

What’s there to see and do in Eastport?

While exploring the area, visit family-friendly sights like Long Island Game Farm, or get outside and enjoy nature at Moriches Bay. Westhampton Beach Performing Arts Center and Smith Point County Park are a couple of places you'll find in the wider area.

What’s a holiday rental in Eastport like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Eastport. Holiday rentals offer extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for a family trip.