Orient Point Holiday Rentals

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Holiday Rentals in Orient Point

Aparthotel in Montauk

3.5 star property
9.2 out of 10, Wonderful, (1265)
"Great ambience. Very kind and friendly service. Wonderful luxe suite. Very homey and cozy. I really enjoyed my stay here. Just lovely. "
United States
Violet
The price is AU$268
includes taxes & fees
8 Dec - 9 Dec
Montauk Manor

Aparthotel in Greenport

3.0 star property
9.0 out of 10, Wonderful, (249)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums

Apartment in New London

10.0 out of 10, Exceptional, (7)
"We had a good experience staying with host, William. Going in and out of our unit was easy with the codes provided. The croissants provided for breakfast were large and delicious. We would stay there again."
United States
Ronald H.
The price is AU$186
includes taxes & fees
8 Dec - 9 Dec
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

Cabin in East Lyme

10.0 out of 10, Exceptional, (123)
"5-star lake view. Amazing stay. we absolutely enjoyed visiting this farm every year. "
United States
Mariya S.
Rustic Lakeside Cabin at White Gate Farm

Holiday Home in Waterford

10.0 out of 10, Exceptional, (17)
"We stayed at the Thames River House after our wedding with friends and it was the perfect spot. The home was beautiful, very clean, and had everything we needed for a relaxing and memorable stay. Couldn’t have asked for a better experience!"
United States
Brandon W.
The price is AU$930
includes taxes & fees
8 Dec - 9 Dec
Thames River Retreat · CT College+Casinos+USCGA

Apartment in New London

9.6 out of 10, Exceptional, (12)
"William was very thorough with our check in and a pleasure to deal with"
United States
Catherine
The price is AU$186
includes taxes & fees
8 Dec - 9 Dec
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

Holiday Home in Sag Harbor

10.0 out of 10, Exceptional, (89)
"House that has everything you need for a wonderful getaway! Excellent communication with the property owner. Thank you Jay for everything and your hospitality! "
United States
Maria R.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Holiday Home in New London

8.0 out of 10, Very good, (16)
"Easy access. We loved our short stay. I would return again. "
United States
Suzanne M.
The price is AU$289
includes taxes & fees
15 Dec - 16 Dec
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

Holiday Home in East Hampton

9.8 out of 10, Exceptional, (74)
"Outstanding house, beautifully maintained and well stocked, with great location."
United States
Jason C.
Stunning Hampton Holiday Family Fantasy for your Team

Holiday Home in Groton

10.0 out of 10, Exceptional, (15)
"Everything was as expected—recommend this location for easy access to Mystic!"
United States
Patrick K.
The price is AU$641
includes taxes & fees
1 Jan - 2 Jan 2026
Oak Grove Cottage - in the foothills of Mystic

Apartment in New London

9.4 out of 10, Exceptional, (10)
"It was the perfect little place for a night away from the kids. "
United States
Tonya B.
The price is AU$672
includes taxes & fees
8 Dec - 9 Dec
Cozy Coastal Cottage New London

Cottage in Waterford

2.0 star property
10.0 out of 10, Exceptional, (14)
"The property was amazing. The house was very clean and the game room was really fun. It was a very cute place and the backyard was perfect for sitting outside in the afternoon. The beds were really soft and comfortable as well."
United States
Jorie M.
The price is AU$476
includes taxes & fees
8 Dec - 9 Dec
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

Apartment in Clinton

9.2 out of 10, Wonderful, (7)
"Everything was as advertised or better. Lovely quiet area near beautiful beaches and great restaurants. We had a terrific experience. "
United States
Tom S.
The price is AU$396
includes taxes & fees
8 Dec - 9 Dec
Shoreline Oasis

Holiday Home in Southampton

9.8 out of 10, Exceptional, (32)
"This place was so nice and so close to so many fun places! "
United States
Daniella L.
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

Apartment in Madison

10.0 out of 10, Exceptional, (36)
"We had a wonderful time here!! "
United States
Leslie S.
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Villa in New London

10.0 out of 10, Exceptional, (45)
"Comfortable and very spacious house - was great for our family reunion. Close to lots of fun things and nice views of water. "
United States
zachary b.
The price is AU$1,407
includes taxes & fees
8 Dec - 9 Dec
Luxury 8BR Winter Wonderland • Sleeps 22 • Indoor Fireplaces & Ocean Views

Condo in Montauk

3.5 star property
9.0 out of 10, Wonderful, (236)
"Great place to stay for small family "
United States
DongHo
Driftwood Resort

Holiday Home in East Hampton

10.0 out of 10, Exceptional, (95)
"Great stay and great communication! "
United States
Nicole S.
Mid-Century Home with Pool, Private Beach Access, and Long-Stay Summer Savings

Condo in Downtown Montauk

4.5 star property
The price is AU$996
includes taxes & fees
8 Dec - 9 Dec
Offshore Residences

Holiday Home in Groton

10.0 out of 10, Exceptional, (126)
"We had an amazing stay at Merritt farm! The host was super accommodating and the house was perfect for our family. Hope has made sure the house has all the comforts of home and is decorated beautifully! The location is a great home base to explore this beautiful area. We would highly recommend staying here and we hope to return. "
United States
Robin G.
The price is AU$687
includes taxes & fees
14 Dec - 15 Dec
Unique Retreat w/ Private Patio, 4 King Beds & BBQ
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 Orient Point Hotel Reviews

Find out more about Orient Point

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

Orient Point holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Orient Point. 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 Orient Point 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 Orient Point holiday rentals we have selected for you start as low as AU$186 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Orient Point rentals

At Expedia, we put the best Orient Point 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 Orient Point 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 Orient Point 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 Orient Point. 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 Orient Point?

Yes, there are holiday rentals close to the most popular sights in Orient Point, or you can select a more secluded option if you're looking for a relaxing stay. Orient Point is known for its waterfront and parks.

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

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA: This holiday home rental outside of Orient Point is located next to a golf course, and offers a garden, air conditioning and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Orient Point?

With 12 Expedia holiday rentals, you're guaranteed to find just the right place for your Orient Point stay.

What’s there to see and do in Orient Point?

Orient Point County Park and Little Bay are a couple of lovely local spots to get outside and enjoy nature. Orient Beach State Park and Kontokosta Winery are a couple of places you'll find in the wider area.

What’s a holiday rental in Orient Point like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Orient Point. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.