Orient Point Holiday Rentals

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Holiday Rentals in Orient Point

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1261)
"Idillic property, very relaxing, with a wonderful view. We stayed only one night so we did not try the restaurant or the pool but we enjoyed the stay. "
United States
Lydia
The price is NZ$315
includes taxes & fees
1 Dec - 2 Dec
Montauk Manor

Montauk Oceanside Suites

3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (417)
"We loved it, suite size was great! "
United States
Patrick
Montauk Oceanside Suites

Cliffside Resort Condominiums

3.0 star property
Greenport
9.0 out of 10, Wonderful, (247)
"Location good. Room could use some renos."
United States
Laura
Cliffside Resort Condominiums

Rustic Lakeside Cabin at White Gate Farm

East Lyme
10.0 out of 10, Exceptional, (123)
"Beautiful cabin on the lake. Will definitely stay again. Easy check-in easy check out. You wont regret staying here!"
United States
James N.
Rustic Lakeside Cabin at White Gate Farm

Driftwood Resort

3.5 star property
Montauk
9.0 out of 10, Wonderful, (235)
"Great place for families and to enjoy the beauty of Montauk without being in Montauk town. Beautiful beach next to a state park so feels secluded and not crowded. Highly recommend!!!"
United States
Angel
Driftwood Resort

1-bedroom cottage with Grove Beach 🏖️ access.

Clinton
9.2 out of 10, Wonderful, (36)
"Host was very friendly and accommodating"
United States
Monika M.
The price is NZ$390
includes taxes & fees
17 Nov - 18 Nov
1-bedroom cottage with Grove Beach 🏖️ access.

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

East Lyme
10.0 out of 10, Exceptional, (106)
"We had such an amazing time here and are planning to return for our next family vacation! The house was clean and spacious and the communication was phenomenal. Everyone we interacted with at the farm was kind, caring, and helpful. There is so much to do at the farm and in the surrounding area. We could not recommend this place more! Best vacation ever!"
United States
Adrienne N.
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

Oak Grove Cottage - in the foothills of Mystic

Groton
10.0 out of 10, Exceptional, (15)
"This place was very comfortable and welcoming. I really dont have anything bad to say about this home. It is very well stocked, extra towels, to soaps, shampoos, conditioners in the bathroom. Extra beach towels, sunscreen if it was needed. Ive stayed at some wyndham condos that arent as well stocked on supplies. Will definitely be returning for a longer stay. "
United States
Jen L.
The price is NZ$770
includes taxes & fees
15 Nov - 16 Nov
Oak Grove Cottage - in the foothills of Mystic

Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

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 NZ$215
includes taxes & fees
12 Nov - 13 Nov
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Sag Harbor
10.0 out of 10, Exceptional, (89)
"Great house with awesome backyard, host responsive and very easy to work with! Would stay again!"
United States
Kilee B.
Grab a Fun Fall Weekend by Wolffer Vineyard! Columbus Day Holiday Now Available

Unique Retreat w/ Private Patio, 4 King Beds & BBQ

Groton
10.0 out of 10, Exceptional, (126)
"The rooms were all equally size with King size beds so it’s perfect for 4 couples. House is warm, clean and comfortable. Would love to come back during warmer months to enjoy the deck and all the house has to offer. Thank you"
United States
Shirley T.
The price is NZ$882
includes taxes & fees
12 Nov - 13 Nov
Unique Retreat w/ Private Patio, 4 King Beds & BBQ

Offshore Residences

4.5 star property
Downtown Montauk
The price is NZ$1,143
includes taxes & fees
13 Nov - 14 Nov
Offshore Residences

Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

New London
9.6 out of 10, Exceptional, (12)
"Bill was an amazing host, he went above and beyond to make our stay as enjoyable as humanly possible I'd highly recommend this place to anyone who is looking to visit the Mystic and New London Connecticut area l."
United States
CJ
The price is NZ$215
includes taxes & fees
12 Nov - 13 Nov
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

Montauk
9.4 out of 10, Exceptional, (40)
"we had a lovely stay in this apartment! it was very spacious and comfortable. The pull out couch was also surprisingly very comfy! Mark and Nancy were very responsive and helpful. "
United States
Madison
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound

Shoreline Oasis

Clinton
9.2 out of 10, Wonderful, (7)
"Cute apartment in a house, separate from the hosts space downstairs. Clean and walking distance to some great harbor-front restaurants. 1 bed and 2 couches (no pull-out couch)"
United States
Molly H.
The price is NZ$462
includes taxes & fees
13 Nov - 14 Nov
Shoreline Oasis

The Surf Club

3.5 star property
Montauk
8.6 out of 10, Excellent, (280)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The Surf Club

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

East Hampton
10.0 out of 10, Exceptional, (95)
"Property was great! Rick was super responsive. It was a great trip to the Hamptons! "
United States
colin f.
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Madison
10.0 out of 10, Exceptional, (36)
"The place was adorable and spotless, the beds were super comfortable it was perfect and a minute from the beach! We will be back. Thanks for a great time!"
United States
Edward
The price is NZ$490
includes taxes & fees
12 Nov - 13 Nov
Walk to Beach! Modern Carriage House - Near Town - Deck, Fire Pit & Grassy Lawn

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Old Saybrook
10.0 out of 10, Exceptional, (34)
"Enjoyed our stay"
United States
Nicole L.
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

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
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 favorite 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 depends 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 NZ$215 per night. Entering your travel dates in the search wizard you might find 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?

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food: This holiday home rental outside of Orient Point is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 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 patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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.