Orient Holiday Rentals

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Holiday Rentals in Orient

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1115)
"Nice, pleasant, staff was warm and friendly "
The price is AU$266
includes taxes & fees
24 Feb - 25 Feb
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (362)
"I didn’t realize the property was mobile check-in and that all communication would be automated in the winter season. if you guys had that more clear on the Expedia it would be awesome. Otherwise the stay was great, clean room, no hassle to get in, right by the beach. "
The price is AU$218
includes taxes & fees
27 Feb - 28 Feb
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (271)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning. "
The price is AU$271
includes taxes & fees
20 Mar - 21 Mar
Windward Shores Ocean Resort

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (251)
"The pictures of the property showed the bed in the bedroom facing the window with direct ocean views I was dis appointed to find out the bed was moved and no longer faced the ocean view."
The Surf Club

Stunning Hampton Holiday Family Fantasy for your Team

9.8 out of 10, Exceptional, (66)
"Great home"
Stunning Hampton Holiday Family Fantasy for your Team

Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

8.6 out of 10, Excellent, (26)
"I recently had the pleasure of spending time at a vacation house in Stonington, Connecticut, and I cannot express enough how fantastic our stay was. This property exceeded all of our expectations and provided our family with a truly memorable experience.From the moment we arrived, we were captivated by the stunning water views. The house is perfectly situated to showcase the beauty of the surrounding landscape, and we found ourselves mesmerized by the sunsets over the water each evening. It was...
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

9.8 out of 10, Exceptional, (98)
"Had a great experience at this property!"
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

Lakeside cottage overhanging the water, beautiful window views across the lake

9.8 out of 10, Exceptional, (195)
"We stayed here as it was close to our daughters cheer Comp and it happened to be my husbands birthday weekend so we wanted to stay somewhere other than a hotel. We enjoyed the hot tub! The view of the lake, the fire pit, the spacious downstairs to watch tv and play family games! Very easy check in. Would recommend, we’d like to come back when weather is warmer to enjoy the lake "
The price is AU$429
includes taxes & fees
25 Feb - 26 Feb
Lakeside cottage overhanging the water, beautiful window views across the lake

Beautiful 2 Bedroom Boho Retreat in Downtown Mystic

10.0 out of 10, Exceptional, (22)
"We visited to celebrate a birthday. The space was perfect for the 4 of us. The location was great as well, walking distance to downtown. We all enjoyed ourselves and loved the decor and snacks left by the host. They even left a birthday present for our friend! We will definitely be back!"
The price is AU$308
includes taxes & fees
25 Feb - 26 Feb
Beautiful 2 Bedroom Boho Retreat in Downtown Mystic

Amazing Ocean Front 2 Story Home, Steps Away From The Water

9.8 out of 10, Exceptional, (90)
"The property was perfect for our vacation with amazing views. I was born & raised in Westerly but moved away. My family still lives in the area & my husband’s lives about 1-1/2hrs away. We flew in to spend Xmas w/our family & hosted Xmas day at the house. It was just what we needed. Big open floor plan, beautiful view of the beach & family. Also Cynthia was amazing!! She put up a tree for us, answered any questions we had, took care of emptying the trash/recycling when full & even let us extend...
Amazing Ocean Front 2 Story Home, Steps Away From The Water

3-bedroom vacation home just a 5-min walk to Main Street, Mystic

10.0 out of 10, Exceptional, (57)
"We were a group of 50 something ladies and lifelong friends. The home was absolutely perfect. All of the 3 bedrooms have their dedicated bathrooms. The kitchen could not be more equipped, including glassware for follow and he TV, heat, appliances "
3-bedroom vacation home just a 5-min walk to Main Street, Mystic

Newly Renovated Montauk Condo with Ocean Views!

9.8 out of 10, Exceptional, (75)
"Montauk has been our Happy Place for many years. We feel fortunate to have discovered this charming condo. Comfortable-feels like home. Immaculate. Consideration went into the details. Luxurious towels. Fantastic location near beach. And owner is a pleasure, right on top of communication. This place made our visit even Happier. Highly recommend. Thank You! Lynn"
Newly Renovated Montauk Condo with Ocean Views!

Charming Historic House in Downtown Mystic

10.0 out of 10, Exceptional, (129)
"This was a 10 out of 10 stay for us. The home was immaculate, stocked with everything you could need to feel at home. Very comfy beds and linens. Fantastic location and great hosts. Would definitely stay at this home again."
The price is AU$517
includes taxes & fees
16 Mar - 17 Mar
Charming Historic House in Downtown Mystic

Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!

10.0 out of 10, Exceptional, (2)
"Lovely to be away in a spot just hidden enough to be accessible from the main road but not close to it. Near to the beach but not on top of it. Perfect! Quiet, woody, peaceful, restful and pet friendly. A hidden gem. The only thing I regret is not having time to stay longer."
Montauk Cozy Beach Studio. Walk to private ocean beach & always pet friendly!

Montauk Mansion INDOOR + OUTDOOR POOLS

9.6 out of 10, Exceptional, (88)
"Well kept unit. Easy access. Very quiet. Pool and spa area beautiful "
Montauk Mansion INDOOR + OUTDOOR POOLS

adorable ranch in beach community

10.0 out of 10, Exceptional, (44)
"Beautiful location, lovely neighbors. House is dated as seen in photos. "
adorable ranch in beach community

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (214)
"We were visiting our so. And just needed an inexpensive..relatively..place to stay….. this was quite convenient…. We had a good night sleep…took a walk to beach..had a great chat with one of the ‘beach boys’ and thought it was lovely……"
Driftwood Resort

Summer 2025 Now Available! Wolffer Vineyard Close!

10.0 out of 10, Exceptional, (83)
"Our stay was amazing! The house was fabulous, beautifully appointed, very clean, private and secluded. Lots to do in the area. Jay was very responsive and helpful when we had questions. Would definitely stay again. "
Summer 2025 Now Available! Wolffer Vineyard Close!

Spacious 7-bedroom house Stonington with amazing views.

Spacious 7-bedroom house Stonington with amazing views.

Classic East Hampton 5 BR in Private Beach Community.Pool, HotTub & Pirate Ship

10.0 out of 10, Exceptional, (80)
"The property was exactly as explained and all in our group loved the place. The house was clean and spacious with plenty of space to rekax."
Classic East Hampton 5 BR in Private Beach Community.Pool, HotTub & Pirate Ship
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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Other types of properties in Orient you may be interested in

Spark by Hilton Mystic Groton

3.0 star property
8.4 out of 10, Very good, (784)
"Clean rooms, nice location, would stay again "
The price is AU$137
includes taxes & fees
27 Feb - 28 Feb
Spark by Hilton Mystic Groton

Hyatt Place Uncasville - Casino Area

3.0 star property
9.2 out of 10, Wonderful, (2335)
"Free breakfast was a nice amenity but the food was awful. Staff was great and place was clean. "
The price is AU$179
includes taxes & fees
27 Feb - 28 Feb
Hyatt Place Uncasville - Casino Area

Best Western Mystic Hotel

2.5 star property
8.8 out of 10, Excellent, (118)
"Very clean! Staff very nice and professional!! 2nd time staying there!!"
The price is AU$179
includes taxes & fees
23 Feb - 24 Feb
Best Western Mystic Hotel
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.

Frequently asked questions

Can I find holiday rentals in Orient?

Yes, there are holiday rentals close to the most popular sights in Orient, or you can select a more secluded option if you're looking for a relaxing stay. Orient is known for its waterfront and golf courses. Make sure you have time to check out the parks and bars during your trip.

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

Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages: This holiday home rental outside of Orient is located by the ocean, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 10 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?

With 22 Expedia holiday rentals, you're guaranteed to find just the right place for your Orient stay.

What can I see and do in Orient?

Orient Beach State Park and Orient Point County Park are a couple of scenic spots to enjoy the outdoors, whereas Oysterponds Historical Society is one of the cultural attractions. While here, Island's End Golf & Country Club and Truman's Beach are other places worth a visit.

What are holiday rentals like in Orient?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Orient. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.