Orient Point Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Orient Point holiday rentals

Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (19 reviews)
"Great stay & great staff!"
United States
James
The price is HK$2,327
HK$2,659 total
includes taxes & fees
7 Jun - 8 Jun
North Fork Resort
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (253 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is HK$1,754
HK$2,345 total
includes taxes & fees
22 Jun - 23 Jun
Cliffside Resort Condominiums
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,355 reviews)
"Had a wonderful stay"
United States
Meghan
The price is HK$1,875
HK$2,295 total
includes taxes & fees
3 Jun - 4 Jun
Montauk Manor
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (313 reviews)
"We always stay at the Windward Shores when we go to Montauk. It is a beautiful, clean and comfortable place, and the price is great!"
United States
Joseph
The price is HK$1,866
HK$2,345 total
includes taxes & fees
7 Jun - 8 Jun
Windward Shores Ocean Resort
Living area

The Surf Club

The Surf Club
3.5 star property
Montauk
8.6 out of 10, Excellent, (282 reviews)
"Quiet, relaxing place to stay, great access to the beach and town!"
United States
Erica
The price is HK$1,797
HK$2,479 total
includes taxes & fees
3 Jun - 4 Jun
The Surf Club
Individually decorated, individually furnished, free WiFi, bed sheets

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (240 reviews)
"Very close to beach"
United States
Rabia
The price is HK$1,484
HK$1,951 total
includes taxes & fees
1 Jun - 2 Jun
Driftwood Resort
Property grounds

Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only

Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only
West Mystic
10.0 out of 10, Exceptional, (3 reviews)
"We had a lovely experience in West Mystick at the Harbor House. The rental was lovely, clean, and contained enough of the necessary amenities. The view of the harbor was lovely. There were renters below us that had small children and at times that was very noisy. You could hear them running back and forth most of the evening. If they were playing music you could hear that as well. It was very cold during our time in Mystic so the heat was necessary. The baseboard heat was sufficient to keep...
United States
Suzanne S.
The price is HK$2,743
HK$3,546 total
includes taxes & fees
1 Jun - 2 Jun
Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only
Beach nearby, sun-loungers, beach towels

Beach Cottage, private beach and pass

Beach Cottage, private beach and pass
East Lyme
10.0 out of 10, Exceptional, (11 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is HK$3,048
HK$5,421 total
includes taxes & fees
3 Jun - 4 Jun
Beach Cottage, private beach and pass
Interior

Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage

Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage
West Mystic
10.0 out of 10, Exceptional, (22 reviews)
"Cute, clean, and perfect little place for an overnight visit :)"
United States
Anonymous traveller
The price is HK$1,959
HK$2,535 total
includes taxes & fees
3 Jun - 4 Jun
Harbor View Landing, Mystic CT - The Block Island Waterfront Cottage
Bathroom

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (426 reviews)
"Awesome room!!! Wish I could come back in the summer"
United States
Nicki
The price is HK$1,688
HK$2,014 total
includes taxes & fees
3 Jun - 4 Jun
Montauk Oceanside Suites
Terrace/patio

Thames River Retreat · CT College+Casinos+USCGA

Thames River Retreat · CT College+Casinos+USCGA
Waterford
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful view of the waters and lots ofcroom to relax."
United States
Omar
The price is HK$3,091
HK$6,612 total
includes taxes & fees
3 Jun - 4 Jun
Thames River Retreat · CT College+Casinos+USCGA
Outdoor pool, a heated pool

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard

Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Sag Harbor
The price is HK$4,410
HK$8,684 total
includes taxes & fees
2 Jun - 3 Jun
Designer Sag Harbor Home w/ Pool + Fire Pit + Yard
Exterior

Downtown Mystic Waterfront Oasis

Downtown Mystic Waterfront Oasis
Mystic River Historic District
10.0 out of 10, Exceptional, (17 reviews)
"Great stay within minutes from downtown Mystic. Definitely coming back!"
United States
Jessica D.
The price is HK$5,094
HK$7,598 total
includes taxes & fees
15 Jun - 16 Jun
Downtown Mystic Waterfront Oasis
Living area

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is HK$11,708
HK$15,283 total
includes taxes & fees
1 Jun - 2 Jun
Cozy 5 Bedroom With Wi-fi And Air Condition
Dining

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Westbrook Center
9.4 out of 10, Exceptional, (3 reviews)
"We had a lovely time during our stay. The hosts were excellent with communication and quick responses throughout our stay. The 2 family suites were perfect for our families to all stay together during this trip. We would definitely book again! "
United States
Kate G.
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water
Private kitchen

Charming 2-bedroom house with WiFi, AC in lovely Waterford

Charming 2-bedroom house with WiFi, AC in lovely Waterford
Waterford
10.0 out of 10, Exceptional, (1 review)
"The home was very clean and welcoming."
United States
Michelle M.
The price is HK$1,411
HK$3,191 total
includes taxes & fees
1 Jun - 2 Jun
Charming 2-bedroom house with WiFi, AC in lovely Waterford
Property grounds

Boutique 3-bedroom cottage, 2 separate units located in Waterford close to beach

Boutique 3-bedroom cottage, 2 separate units located in Waterford close to beach
Waterford
The price is HK$3,644
HK$6,986 total
includes taxes & fees
4 Jun - 5 Jun
Boutique 3-bedroom cottage, 2 separate units located in Waterford close to beach
Microwave, oven, stovetop, dishwasher

Entire Vacation Home in Waterford Connecticut

Entire Vacation Home in Waterford Connecticut
Waterford
8.8 out of 10, Excellent, (3 reviews)
"Such a nice quiet property in Waterford, short distance away from many local restaurants and shops and 20 minutes away from the casino. "
United States
Elise Marie K.
The price is HK$1,724
HK$3,652 total
includes taxes & fees
1 Jun - 2 Jun
Entire Vacation Home in Waterford Connecticut
Smart TV, fireplace, video games, DVD player

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

Unique Retreat w/ Private Patio, 4 King Beds & BBQ
Groton
10.0 out of 10, Exceptional, (131 reviews)
"The house was very clean. We thoroughly enjoyed our stay. The host was very communicative and provided everything we needed. Thank you!"
United States
Karolina Z.
The price is HK$2,164
HK$4,824 total
includes taxes & fees
4 Jun - 5 Jun
Unique Retreat w/ Private Patio, 4 King Beds & BBQ
Exterior

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.4 out of 10, Exceptional, (46 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
The price is HK$2,652
HK$4,934 total
includes taxes & fees
1 Jun - 2 Jun
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
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

Offshore Montauk

Offshore Montauk

10/10 Excellent
"Great experience!"
Kerron 1-night trip
Posted 5 hours ago
Offshore Montauk

Find out more about Orient Point

Search for holiday rentals in Orient Point on Expedia! You can easily find your home rentals, villas, holiday apartments in Orient Point using one of the methods below:

  • View our selection of featured holiday rentals in Orient Point
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  • Enter your travel dates to view the best deals on holiday rentals in Orient Point while they last

Look no further and take a look at our great range of rental properties in Orient Point!

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?

11 Bedroom Tranquil Waterfront Getaway: This holiday home rental outside of Orient Point is located on the waterfront, and has a balcony, a garden 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. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Orient Point?

With 8 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 Gardiner's Bay Country Club 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.