Photo by Dana D'angelo

Holiday Rentals in Eastport

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Eastport

11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

9.6 out of 10, Exceptional, (33)
"We had a amazing stay and plan to come back next July again"
11-Bedroom Mansion with an Seasonal Outdoor Pool 10.5 bathrooms

Canoe Place Waterfront Residences

4.0 star property
The price is €2,097
includes taxes & fees
23 Jun - 24 Jun
Canoe Place Waterfront Residences

Meets Modern Comfort in This 3-Bedroom Long Island Sound Retreat

9.0 out of 10, Wonderful, (2)
"We spent two nights at Roman’s house and it was perfect for our needs. He was communicative and helpful when any questions arose and explained everything perfectly to help make our stay a pleasant one. I highly recommend staying here!"
Meets Modern Comfort in This 3-Bedroom Long Island Sound Retreat

East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

10.0 out of 10, Exceptional, (88)
"Place was beautiful. It was very clean. Easy to get to. Would stay again"
The price is €642
includes taxes & fees
6 Jul - 7 Jul
East End cottage on water! Outdoor tub&shower! Minutes from Hamptons & wineries.

Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

10.0 out of 10, Exceptional, (5)
"Michael's cottage was incredibly well-appointed. The location to Southampton, Coopers Beach and neighboring townships made this very convenient for my trip. The true star of this cottage is the upstairs deck which was perfect for relaxing and stargazing. I will certainly return next summer. "
Charming Two-Story Retreat in Southampton Village walk to town, beach and train.

Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

10.0 out of 10, Exceptional, (102)
"The house and stay were great!"
Beachy Chic South of the Hwy in SH Village just 3blks to shops, food and fun!!!🏖️

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

10.0 out of 10, Exceptional, (181)
"Everything was amazing, the house is beautiful and very spacious, and the host was very friendly! I would 100% stay here again! "
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr

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

9.6 out of 10, Exceptional, (37)
"Lovely cottage beautifully decorated, close to restaurants, farm stands, and food stores. A least a 15 to 20 minute walk to the beach."
The price is €361
includes taxes & fees
2 Jul - 3 Jul
Renovated Cozy Chic North Fork Cottage, steps away from the Beach & Wine Trail!!

Quiet Bayside cottage. 10 minutes to beach, 15 minutes to shopping.

8.4 out of 10, Very good, (11)
"Wonderful location, love the brine scented air & cattails. Perfect location for us to easily visit family. Really enjoyed the relaxing weekend. Will definitely try to stay there again. "
The price is €153
includes taxes & fees
23 Jun - 24 Jun
Quiet Bayside cottage. 10 minutes to beach, 15 minutes to shopping.

Location and views! Located directly on Shinnecock Bay!

9.0 out of 10, Wonderful, (26)
"Stay was relaxing, space was very cozy. we enjoyed our stay. "
The price is €530
includes taxes & fees
23 Jun - 24 Jun
Location and views! Located directly on Shinnecock Bay!

10 Bedroom Hampton House with a regulation size Pickleball court

9.8 out of 10, Exceptional, (26)
"Had so much fun this weekend in Hampton Bays! House was perfect for a group of friends - many bedrooms, bathrooms, great pool with tons of outdoor games, and even the arcade room inside! So close to the beach, and a number of great restaurants. Highly recommend this house, and appreciate how helpful our host was with making sure we had everything we need and more!"
10 Bedroom Hampton House with a regulation size Pickleball court

Walk to Beach 2BR Near Dining & Shopping

6.6 out of 10, (13)
"a little hard to find: hint, look for the address on the garbage cans, because the addresses get a bit wonky further down the block, but this is a lovely spot on the north shore if all you're looking for is a clean bed on a quiet street, and the two bedrooms are so much better for friends or families than would be two rooms in the hotel by the highway -- oh, and there's a nice bagel place just north of the Starbucks on the corner of 25A"
The price is €274
includes taxes & fees
23 Jun - 24 Jun
Walk to Beach 2BR Near Dining & Shopping

1856 Trading House w/ walk to water

9.6 out of 10, Exceptional, (46)
"We've stayed here twice when visiting family in town, it's a lovely space and very welcoming."
1856 Trading House w/ walk to water

Chic Hampton Bays escape with private pool, expansive sundeck, and seamless...

Chic Hampton Bays escape with private pool, expansive sundeck, and seamless...

Hamptons Oasis! Huge Heated Pool, Games, Fenced Yard

10.0 out of 10, Exceptional, (1)
"Very relaxing and neat place for a family gateway "
Hamptons Oasis! Huge Heated Pool, Games, Fenced Yard

Cozy Country Cottage #3

10.0 out of 10, Exceptional, (20)
"This is our second time and the cottages are well equipped with everything you need. They are very cozy, we especially enjoyed the fireplace/heater in the cool evenings."
The price is €269
includes taxes & fees
24 Jun - 25 Jun
Cozy Country Cottage #3

Southampton cozy cottage by the beach

The price is €520
includes taxes & fees
26 Jun - 27 Jun
Southampton cozy cottage by the beach

Charming and Bright Cottage with Salt Water Pool

10.0 out of 10, Exceptional, (5)
"What a beautiful cottage. Clean and bright. Would definitely stay again!"
Charming and Bright Cottage with Salt Water Pool

Cozy Country Cottage #4

10.0 out of 10, Exceptional, (8)
"This place checked all of our boxes. It was clean, comfortable, and had everything we needed. We will definitely stay here again when we come back."
The price is €269
includes taxes & fees
23 Jun - 24 Jun
Cozy Country Cottage #4

Summer getaway

9.2 out of 10, Wonderful, (10)
"Beautiful home with a beautiful pool"
Summer getaway
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.
Save an average of 15% on thousands of hotels when you're signed in

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 10 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.