Orient Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Orient holiday rentals

Terrace/patio

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 HK$1,576
HK$2,141 total
includes taxes & fees
31 May - 1 Jun
Cliffside Resort Condominiums
Flat-screen TV

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
"Great stay & great staff!"
United States
James
The price is HK$2,067
HK$2,361 total
includes taxes & fees
1 Jun - 2 Jun
North Fork Cottages & RV Resort
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, (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 HK$1,247
HK$1,637 total
includes taxes & fees
18 May - 19 May
Windward Shores Ocean Resort
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,343 reviews)
"Had a wonderful stay"
United States
Meghan
The price is HK$1,184
HK$1,506 total
includes taxes & fees
25 May - 26 May
Montauk Manor
Smart TV

The Tiny Cottage on The Pond

The Tiny Cottage on The Pond
Oakdale,
10.0 out of 10, Exceptional, (8 reviews)
"Host was extremely nice and responsive. Cottage is so cute I can't wait to come back in the summer! Nice and private little place and adorable goats! If you're looking for a quiet, cute little getaway this is the place to go! Thank you Thomas for the hospitality!!"
United States
Sharon O.
The price is HK$881
HK$1,169 total
includes taxes & fees
18 May - 19 May
The Tiny Cottage on The Pond
1 bedroom, desk, iron/ironing board, travel cot

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (41 reviews)
"We had such a wonderful one night stay at Shalom Cottage! The place was absolutely beautiful—so cozy, clean, and thoughtfully decorated. Raj, the host was truly amazing! He was kind, responsive, and made sure we had everything we needed from start to finish. We felt so welcomed and comfortable the entire time. We would definitely love to stay here again and highly recommend it to anyone! "
United States
Alexis F.
The price is HK$965
HK$1,837 total
includes taxes & fees
18 May - 19 May
1-bedroom cottage with Grove Beach 🏖️ access.
Smart TV, books

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Stonington
9.8 out of 10, Exceptional, (178 reviews)
"A bright and cozy vibe as well as being thoroughly equipped with everything to make our stay comfortable.We appreciated the winter escape and enjoyed Stonington, Mystic, and Westerly. A lovely stay!"
United States
Dawn R.
The price is HK$744
HK$1,975 total
includes taxes & fees
18 May - 19 May
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Smart TV, books

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 HK$1,150
HK$3,743 total
includes taxes & fees
19 May - 20 May
Rogers Lake House (87) · CT College+Beach+USCGA
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$1,253
HK$2,985 total
includes taxes & fees
18 May - 19 May
Charming 2-bedroom house with WiFi, AC in lovely Waterford
1 bedroom, free WiFi, bed sheets

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is HK$1,076
HK$2,101 total
includes taxes & fees
10 Jun - 11 Jun
Lakefront Boho Tiny House
1 bedroom, desk, iron/ironing board, free WiFi

The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is HK$1,150
HK$2,236 total
includes taxes & fees
26 May - 27 May
The Stern at Soundview · Beach+Ocean+Sunrise
Property grounds

Driftwood Resort

Driftwood Resort
3.5 star property
Montauk
9.0 out of 10, Wonderful, (237 reviews)
"Wonderful location, right on the beach. The staff was kind and welcoming. The property was beautiful with a pool, playground, tennis and basketball courts, cornhole, etc. Very family friendly. Some walkable restaurants nearby and a quick 5-10 minute drive into town where a lot of the restaurants and shops are. We did have ants all in our food one day but the staff addressed it quickly "
United States
John
The price is HK$1,219
HK$1,648 total
includes taxes & fees
18 May - 19 May
Driftwood Resort
Exterior

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 HK$1,240
HK$2,352 total
includes taxes & fees
18 May - 19 May
Cozy Lakefront Tiny House
TV

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!

Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
Montville
10.0 out of 10, Exceptional, (6 reviews)
"great place to stay"
United States
christopher
The price is HK$1,018
HK$2,533 total
includes taxes & fees
18 May - 19 May
Cozy 3-bedroom house near Mystic and Mohegan & Foxwood Casinos!
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$2,811
HK$5,145 total
includes taxes & fees
27 May - 28 May
Beach Cottage, private beach and pass
Property grounds

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

Lakeside cottage ON the water with beautiful views up the lake!
Ledyard
9.8 out of 10, Exceptional, (198 reviews)
"We had a wonderful stay at the cottage! It was so cozy and peaceful, exactly what we were looking for. Mini splits kept our rooms toasty on the cold night, and we had everything we needed. Our host was super communicative and helpful. Would definitely stay here again!"
United States
Anonymous traveller
The price is HK$1,541
HK$2,993 total
includes taxes & fees
19 May - 20 May
Lakeside cottage ON the water with beautiful views up the lake!
Property grounds

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

Lakeside cottage overhanging the water, beautiful window views across the lake
Ledyard
9.8 out of 10, Exceptional, (227 reviews)
"wonderful place to stay. the pond is beautiful. plenty to do nearby "
United States
Mike
The price is HK$1,434
HK$2,765 total
includes taxes & fees
18 May - 19 May
Lakeside cottage overhanging the water, beautiful window views across the lake
Fridge, microwave, oven, stovetop

Upscale Apartment in Mystic 7 Minute Walk to Drawbridge

Upscale Apartment in Mystic 7 Minute Walk to Drawbridge
Stonington
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful, quiet, close to town!! Really enjoyed our stay. "
United States
Maureen F.
The price is HK$1,879
HK$3,241 total
includes taxes & fees
15 May - 16 May
Upscale Apartment in Mystic 7 Minute Walk to Drawbridge
Dining

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.
Adorable Cottage with Cottage porch, walk to water & town
Terrace/patio

Tranquil Farmhouse Retreat

Tranquil Farmhouse Retreat
Montville
9.8 out of 10, Exceptional, (22 reviews)
"We had a great stay during the Thanksgiving holiday. We were able to enjoy the space of the house and the close proximity to Mohegan Sun."
United States
Allison R.
The price is HK$3,131
HK$6,580 total
includes taxes & fees
3 Jun - 4 Jun
Tranquil Farmhouse Retreat
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Orient Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Nice property "
Colleen 1-night trip
Posted 4 hours ago
Water's Edge Resort & Spa

Find out more about Orient

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

  • View our selection of featured holiday rentals in Orient
  • Use the map to find apartments and other holiday homes in the Orient neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Orient while they last

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

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?

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village: This holiday home rental outside of Orient is located near the beach, and has a private garden, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Orient?

With 16 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 Little Bay 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.