Orient Holiday Rentals

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Holiday Rentals in Orient

Orient Village — Historic Bayfront Cottage — 2025 Season

Orient
10.0 out of 10, Exceptional, (23)
"Step away from your busy schedule, step back in time, and step down to the beach. Bayside Cottage is an idyllic, charming, and rare place -- one increasingly harder to find as grandiose properties populate many parts of the Island. Thankfully the North Fork has retained much of its character since we began visiting some 20 years ago, and Orient is beautifully preserved with a lot of tender loving care, especially towards nature. It was turtle season in June! At Bayside, circa 1887, one doesn't...
United States
Jennifer G.
The price is NZ$1,258
includes taxes & fees
30 Nov - 1 Dec
Orient Village — Historic Bayfront Cottage — 2025 Season

Lakefront Boho Tiny House

East Lyme
10.0 out of 10, Exceptional, (3)
"My husband has always wanted to try a tiny house. This place exceeded our expectations. Lovely house. Lovely lake. He was in heaven fishing and kayaking "
United States
Asha A.
The price is NZ$431
includes taxes & fees
18 Nov - 19 Nov
Lakefront Boho Tiny House

Cozy Lakefront Tiny House

East Lyme
10.0 out of 10, Exceptional, (2)
"The bed and pillows were very comfortable. The outside space was very relaxing. Kevin’s place was perfect! We had questions and he replied back right away. We definitely want to go back. "
United States
Rebecca K.
The price is NZ$415
includes taxes & fees
18 Nov - 19 Nov
Cozy Lakefront Tiny House

Charming houseboat in pleasant New London with AC, WiFi

New London, Thamesport
9.6 out of 10, Exceptional, (13)
"Everything was great and as advertised"
United States
Joshua H.
The price is NZ$571
includes taxes & fees
22 Nov - 23 Nov
Charming houseboat in pleasant New London with AC, WiFi

North Fork Cottages & RV Resort

3.0 star property
Greenport
10.0 out of 10, Exceptional, (1)
"Great stay! Very clean and new. Comfy beds, great location "
United States
Lisa
The price is NZ$395
includes taxes & fees
9 Nov - 10 Nov
North Fork Cottages & RV Resort

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
Old Lyme
10.0 out of 10, Exceptional, (3)
"Perfect for a weekend beach getaway. Very small but accurately portrayed in the pictures. It was clean and the host was very helpful and responsive. "
United States
Olivia C.
The price is NZ$343
includes taxes & fees
9 Nov - 10 Nov
The Stern at Soundview · Beach+Ocean+Sunrise

Montauk Manor

3.5 star property
Montauk
9.2 out of 10, Wonderful, (1260)
"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$316
includes taxes & fees
1 Dec - 2 Dec
Montauk Manor

Lakeside cottage ON the water with beautiful views up the lake!

Ledyard
9.8 out of 10, Exceptional, (189)
"every was very easy process and a pleasure to stay there"
United States
Michael H.
The price is NZ$470
includes taxes & fees
7 Dec - 8 Dec
Lakeside cottage ON the water with beautiful views up the lake!

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

Ledyard
9.8 out of 10, Exceptional, (214)
"Well equipped for family fun. Kids had a great time paddling around the lake!"
United States
Kristen A.
The price is NZ$441
includes taxes & fees
1 Dec - 2 Dec
Lakeside cottage overhanging the water, beautiful window views across the lake

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$386
includes taxes & fees
11 Nov - 12 Nov
1-bedroom cottage with Grove Beach 🏖️ access.

A Mystic Stay as Sweet as Apple Pie!

2.0 star property
Old Mystic
10.0 out of 10, Exceptional, (4)
"Property was everything that the listing said it would be. Very accurate description. Unique lovely property with nautical theme decor. The property manager was A with hospitality and communication regarding check in, location etc. Great place to stay when visiting the Mystic Ct area."
United States
dorothy c.
The price is NZ$380
includes taxes & fees
8 Dec - 9 Dec
A Mystic Stay as Sweet as Apple Pie!

Stevedore Landing-#3 · walk downtown Mystic · train · aquarium

Stonington
10.0 out of 10, Exceptional, (4)
"We enjoyed our stay. The apartment is in excellent condition."
United States
Marcell
The price is NZ$379
includes taxes & fees
9 Nov - 10 Nov
Stevedore Landing-#3 · walk downtown Mystic · train · aquarium

New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

Old Mystic
10.0 out of 10, Exceptional, (8)
"Excellent amenities, prompt communication, beautiful area, convenient location, quiet and peaceful. Host went above and beyond."
United States
Shazia L.
The price is NZ$365
includes taxes & fees
10 Nov - 11 Nov
New England Hospitality at the Carriage House Mystic Vacation Rentals LLC

Hidden gem! Southampton beach cottage

Hampton Bays
10.0 out of 10, Exceptional, (1)
The price is NZ$810
includes taxes & fees
16 Nov - 17 Nov
Hidden gem! Southampton beach cottage

Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

Waterford
10.0 out of 10, Exceptional, (9)
"Open concept home beautiful with private yard space. It was perfect for our stay"
United States
Berlyne S.
The price is NZ$636
includes taxes & fees
8 Dec - 9 Dec
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks

The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2

Stonington
10.0 out of 10, Exceptional, (5)
"This cottage/guest house is walking distance to all downtown Mystic has to offer. The property is immaculate and has everything you need to make a weekend getaway be a breeze!"
United States
Anonymous traveller
The price is NZ$400
includes taxes & fees
11 Nov - 12 Nov
The Oar Cottage (24) · walk Mystic-Train/EV Lvl-2

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

Waterford
10.0 out of 10, Exceptional, (1)
"The home was very clean and welcoming."
United States
Michelle M.
The price is NZ$654
includes taxes & fees
17 Nov - 18 Nov
Charming 2-bedroom house with WiFi, AC in lovely Waterford

Super Cute & Cozy Apartment in Downtown Mystic!

Mystic
9.6 out of 10, Exceptional, (79)
"We loved the location as it was very walkable into town. The property has everything you could need and the kitchen was well equipped. The host was very helpful with check in and out times. I would stay here again. "
United Kingdom
peter tolland
The price is NZ$337
includes taxes & fees
10 Nov - 11 Nov
Super Cute & Cozy Apartment in Downtown Mystic!

Montauk Oceanside Suites

3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (416)
"We loved it, suite size was great! "
United States
Patrick
Montauk Oceanside Suites

Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk

2.0 star property
Waterford
10.0 out of 10, Exceptional, (12)
"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 NZ$552
includes taxes & fees
9 Nov - 10 Nov
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
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 Hotel Reviews

Find out more about Orient

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

Orient holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Orient. 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 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 holiday rentals we have selected for you start as low as NZ$214 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Orient rentals

At Expedia, we put the best Orient 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 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 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. 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 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 has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many holiday rentals are there in Orient?

With 20 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 Point County Park and Truman's Beach are a couple of scenic spots to enjoy the outdoors, whereas Oysterponds Historical Society is one of the cultural attractions. While here, Orient Beach State Park and Island's End Golf & Country Club 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.