Orient Point Vacation Rentals

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Our top choices for Orient Point vacation rentals

Thames River Retreat · CT College+Casinos+USCGA

Thames River Retreat · CT College+Casinos+USCGA
Waterford
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful view of the waters and lots ofcroom to relax."
United States
Omar
The price is CA $650
CA $1,300 total
includes taxes & fees
Jun 3 - Jun 4
Thames River Retreat · CT College+Casinos+USCGA

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
"Great stay & great staff!"
United States
James
The price is CA $283
CA $323 total
includes taxes & fees
May 19 - May 20
North Fork Resort

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (252 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is CA $277
CA $376 total
includes taxes & fees
May 31 - Jun 1
Cliffside Resort Condominiums

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (312 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 CA $287
CA $365 total
includes taxes & fees
May 28 - May 29
Windward Shores Ocean Resort

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 CA $549
CA $974 total
includes taxes & fees
May 30 - May 31
Beach Cottage, private beach and pass

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 CA $220
CA $524 total
includes taxes & fees
May 18 - May 19
Charming 2-bedroom house with WiFi, AC in lovely Waterford

Harbor View Landing Mystic, CT - The Nantucket Waterfront Cottage

Harbor View Landing Mystic, CT - The Nantucket Waterfront Cottage
West Mystic
10.0 out of 10, Exceptional, (5 reviews)
"The cottage was beautifully decorated, cozy and made our stay very comfortable. The scenery was spectacular. We will definitely be going back!"
United States
Janet R.
The price is CA $908
CA $1,173 total
includes taxes & fees
May 21 - May 22
Harbor View Landing Mystic, CT - The Nantucket Waterfront Cottage

Entire Vacation Home in Waterford Connecticut

Entire Vacation Home in Waterford Connecticut
Waterford
8.8 out of 10, Excellent, (3 reviews)
"Located so perfectly close to everything we wanted to do on vacation. The house was so clean and comfortable. Communication with the owner was A++. The neighbors were even so friendly and waving/smiling. It felt as if we were home. If we come back to that area again we hope this place will be available. "
United States
Jennifer A.
The price is CA $303
CA $641 total
includes taxes & fees
May 18 - May 19
Entire Vacation Home in Waterford Connecticut

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,346 reviews)
"Had a wonderful stay"
United States
Meghan
The price is CA $370
CA $450 total
includes taxes & fees
Jun 1 - Jun 2
Montauk Manor

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

Harbor View Landing - The Mystic Waterfront House - Second Floor Only
West Mystic
9.6 out of 10, Exceptional, (8 reviews)
"Awesome time, nice and peaceful "
United States
Dion B.
The price is CA $1,492
CA $1,929 total
includes taxes & fees
May 21 - May 22
Harbor View Landing - The Mystic Waterfront House - Second Floor Only

Adorable Cottage with Cottage porch, walk to water & town

Adorable Cottage with Cottage porch, walk to water & town
Westbrook Center
8.8 out of 10, Excellent, (6 reviews)
"Great host and property"
United States
Kevin K.
The price is CA $294
CA $641 total
includes taxes & fees
May 18 - May 19
Adorable Cottage with Cottage porch, walk to water & town

Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (6 reviews)
"Host was very responsive. Property as described. We would stay again! "
United States
john18250
The price is CA $179
CA $631 total
includes taxes & fees
May 18 - May 19
Rogers Lake House (87) · CT College+Beach+USCGA

The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.2 out of 10, Wonderful, (5 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is CA $252
CA $612 total
includes taxes & fees
May 19 - May 20
The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bridge at Soundview · Beach+OceanView+Sunrise

The Bridge at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (2 reviews)
"Great space, large dining area, fully stocked kitchen, large bedrooms, great mattresses, ocean view from deck and one block from the ocean "
United States
Scott F.
The price is CA $443
CA $1,016 total
includes taxes & fees
Jun 2 - Jun 3
The Bridge at Soundview · Beach+OceanView+Sunrise

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
Killingworth
10.0 out of 10, Exceptional, (56 reviews)
"Stayed here for Valentine's weekend with my wife and it was perfect! Gardner and Kathy were great with communication and the cabin itself was beautiful! It had everything we needed for the weekend and the location is close to many nearby attractions. Book your stay at Mapletree Cabin.. you won't regret it! "
United States
Miguel D.
The price is CA $688
CA $1,218 total
includes taxes & fees
Jun 3 - Jun 4
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature

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.
The price is CA $569
CA $1,033 total
includes taxes & fees
May 18 - May 19
Beach Retreat - 5 beds , 2 kitchens @ Salt Island- Westbrook -walk to water

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (3 reviews)
"It was a peaceful and quant "
United States
Patricia M.
The price is CA $188
CA $377 total
includes taxes & fees
May 18 - May 19
Cozy Lakefront Tiny House

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is CA $308
CA $659 total
includes taxes & fees
May 18 - May 19
Adorable Cottage, 5 min walk to water & town

Riverfront Home with a View!

Riverfront Home with a View!
Groton
9.6 out of 10, Exceptional, (80 reviews)
"We enjoyed our time at your home! It’s a beautiful spot on the Thames. Great space to cook and visit with friends and family! "
United States
Kim S.
The price is CA $734
CA $1,305 total
includes taxes & fees
May 18 - May 19
Riverfront Home with a View!

Cozy 5 Bedroom With Wi-fi And Air Condition

Cozy 5 Bedroom With Wi-fi And Air Condition
Wainscott
The price is CA $2,054
CA $2,682 total
includes taxes & fees
May 18 - May 19
Cozy 5 Bedroom With Wi-fi And Air Condition
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Orient Point. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Orient Point?

Yes, there are vacation rentals near top attractions in Orient Point, or you can go with a secluded option if you want a relaxing place to stay. Orient Point is known for its waterfront and parks.

What are some of the best vacation home rentals in Orient Point?

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping: You might want to consider this vacation home rental near Orient Point, which offers an outdoor pool, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Orient Point?

With 9 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Orient Point like?

Vacation rentals are private properties you can stay in for short or long periods in Orient Point. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have a home away from home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family trip.