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Old Greenwich Holiday Rentals

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Holiday Rentals in Old Greenwich

Exterior
Stamford Suites
2.5 star property
6.8 out of 10, (705)
"The hotel suite was larger than I expected. The staff was professional and friendly. The noise from the residential families was a minor nuisance. The halls, elevator, bathroom and common areas where dirty. No hot water or tea bags at breakfast."
The price is AU$261
per night
30 May - 31 May
Stamford Suites
Exterior
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (49)
"Beautiful location and old, well-maintained house. Really perfect for our family group of 17"
Waterfront Retreat Center for Health & Wellness
Private beach nearby, sun-loungers, beach umbrellas, beach towels
DUNE Fairfield Beach
3.0 star property
10.0 out of 10, Exceptional, (10)
"Modern cottage near the beach. Clean and comfortable. Very responsive."
The price is AU$328
per night
23 May - 24 May
DUNE Fairfield Beach
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1 bedroom, in-room safe, desk, iron/ironing board
💎 Modern Chic Getaway, Biz Friendly, Close 2 all 👣
💎 Modern Chic Getaway, Biz Friendly, Close 2 all 👣
Beach
Spacious 3BR Private Home * Direct Water View
10.0 out of 10, Exceptional, (12)
"This is a very nice accommodation. Situated by the beautiful park and water. You can find shopping facilities within walking distance. The landlord was very reliable in making sure that our stay was very nice."
Spacious 3BR Private Home * Direct Water View
Interior
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
10.0 out of 10, Exceptional, (3)
"7 bedrooms, most with water views, were perfect for my siblings and me, our spouses and children, and our mother to spend a glorious weekend together! We hosted an unforgettable 80th bday party for our Mom with all our extended family and friends. Wow! The house is gorgeous! It is perfect for a event. The grand hall, the ability to open up the rooms to the backyard, and the VIEW, truly set the stage for a beautiful evening. The home is truly remarkable! My mom was overwhelmed and so thankful...
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
Beach
Seascape Beach Home- Seas-the-Day at this cozy home on Shippan Point
The price is AU$927
per night
19 May - 20 May
Seascape Beach Home- Seas-the-Day at this cozy home on Shippan Point
Exterior
The Subterranean Haven
10.0 out of 10, Exceptional, (1)
"The neighborhood is really nice and clean with a good variety of stores nearby. We found the subterranean haven to be a great location for unwinding and having small events. The George's are incredibly understanding, patient and flexible. We'd definitely recommend this host to anyone."
The price is AU$310
per night
27 May - 28 May
The Subterranean Haven
Terrace/patio
Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (103)
"Pleasant stay"
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Reception
Global Luxury Suites White Plains
3.5 star property
7.6 out of 10, Good, (17)
"If this option is available in the city you are traveling to, take it! You get a home-y, modern APARTMENT with space, rather than a tiny, old hotel room. I always search Global Luxury Suites before searching anything else."
Global Luxury Suites White Plains
Smart TV
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY
9.4 out of 10, Exceptional, (9)
"The apartment was exactly as stated and shown in the photos"
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY
Fridge, microwave, oven, stovetop
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
10.0 out of 10, Exceptional, (1)
"The owner is a verry nice person!!"
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor
Pool
Luxe Mansion 40 min from Manhattan
The price is AU$2,471
per night
19 May - 20 May
Luxe Mansion 40 min from Manhattan
TV, books
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
The price is AU$534
per night
19 May - 20 May
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Outdoor pool, a heated pool
Westport Paradise With Every Amenity!
10.0 out of 10, Exceptional, (12)
"Super clean, comfortable, and great for overnight stay. Will definitely be back!"
The price is AU$1,218
per night
20 May - 21 May
Westport Paradise With Every Amenity!
Fridge, microwave, oven, stovetop
Luxury penthouse suite
2.0 out of 10, (1)
"it had roaches"
The price is AU$559
per night
17 May - 18 May
Luxury penthouse suite
View from property
Serenity Awaits at this Cozy Lakeside Bungalow
10.0 out of 10, Exceptional, (15)
"We so enjoyed our stay! The house was perfect for our family, conveniently located close to extended family and with the most beautiful view. The house had everything we needed and provided the perfect home base for spring break in our hometown. We even got to experience an earth quake ;) thank you!!"
Serenity Awaits at this Cozy Lakeside Bungalow
Fridge, microwave, oven, stovetop
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
10.0 out of 10, Exceptional, (12)
"Stayed at Coastal Retreat for a weekend visit with son who attends Fairfield University, brought both sets of parents and teen daughter (ages ranging 73-16), plenty of room and able to enjoy a wonderful family dinner with son even in attendance. Wonderful area, close walk to beach and easy to get to downtown Fairfield and university. Very clean and welcoming! Greg was wonderful to work with and answered any question we had that came up both prior and upon arrival. The only thing we would mention...
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center
Outdoor pool, a heated pool
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time
10.0 out of 10, Exceptional, (7)
"GREAT location and house for a family reunion. It had everything that we needed inside and out. Large rooms for entertaining, a beautiful pool and outdoor patio. Very centrally located for shopping, airports, farm stands and yet very quiet. GREAT STAY!"
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time
Fridge, microwave, oven, stovetop
Delightful Entire 2 Bedroom Apartment - 30 min train to NYC
10.0 out of 10, Exceptional, (1)
"AAA++ for place and host"
The price is AU$442
per night
21 May - 22 May
Delightful Entire 2 Bedroom Apartment - 30 min train to NYC
Don't see what you're looking for?
See all available properties in Old Greenwich
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.

Old Greenwich Holiday Home Travel Info

Other types of properties in Old Greenwich you may be interested in

Lobby
Hyatt Regency Greenwich
4.0 star property
7.8 out of 10, Good, (1002)
"Lovely clean room Bed was sparling and comfortable Great location!. "
The price is AU$323
per night
27 May - 28 May
Hyatt Regency Greenwich
Interior
Royal Regency Hotel
3.5 star property
8.0 out of 10, Very good, (1469)
"I recommend this place. I stayed here after attending my best friend’s wedding nearby and I enjoyed it. Parking was complimentary, breakfast was really good and all the staff was amazingly friendly and professional. The room was big, everything was working fine: a/c and hot water. The bed was very comfortable. I definitely would stay here again. "
The price is AU$503
per night
25 May - 26 May
Royal Regency Hotel
Desk, laptop workspace, blackout curtains, iron/ironing board
Baymont by Wyndham White Plains - Elmsford
2.5 star property
8.2 out of 10, Very good, (1004)
"Always clean. Good breakfast, rates are good"
The price is AU$206
per night
27 May - 28 May
Baymont by Wyndham White Plains - Elmsford
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.

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

Old Greenwich holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old Greenwich. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Old Greenwich 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 Old Greenwich holiday rentals we have selected for you start as low as AU$261 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Old Greenwich rentals

At Expedia, we put the best Old Greenwich 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 Old Greenwich 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 Old Greenwich 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 Old Greenwich. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Recent reviews of Old Greenwich properties
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