Old Greenwich Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Old Greenwich holiday rentals

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (76 reviews)
"Location was perfect!"
United States
Linda J P.
The price is NZ$1,011
includes taxes & fees
21 May - 22 May
Captain's Cottage - Cold Spring Harbor Water Views

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Huntington
9.8 out of 10, Exceptional, (7 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is NZ$373
includes taxes & fees
27 May - 28 May
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Bright&Comfy 2bed/1ba in quiet White Plains duplex

Bright&Comfy 2bed/1ba in quiet White Plains duplex
White Plains
8.8 out of 10, Excellent, (6 reviews)
"Location was great! Clean house! Comfy beds! Great space! "
United States
Montana M.
Bright&Comfy 2bed/1ba in quiet White Plains duplex

Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
The price is NZ$1,004
includes taxes & fees
14 May - 15 May
Luxury 3 BR Near NYC with Easy Parking

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (87 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is NZ$443
includes taxes & fees
26 May - 27 May
DUNE Fairfield Beach

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (31 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is NZ$686
includes taxes & fees
25 May - 26 May
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Family Home near NY Beach Private Workspace

Family Home near NY Beach Private Workspace
Glen Head
8.8 out of 10, Excellent, (9 reviews)
"We had another great stay. This was our second time renting and everything was clean, comfortable, and well equipped. The fenced backyard was perfect for our dogs, and the walk to the train made getting into the city very easy. We would happily stay here again and highly recommend this cozy place."
United States
Jeffrey W.
Family Home near NY Beach Private Workspace

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Excellent home, met all expectations, and attentive staff"
United States
Steve G.
The price is NZ$2,971
includes taxes & fees
4 June - 5 June
New Beach Home near Stamford Downtown/Shippan

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (34 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is NZ$539
includes taxes & fees
21 May - 22 May
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
Bronx
9.8 out of 10, Exceptional, (21 reviews)
"Nice home very clean and easy to access transit"
United States
Christina F.
The price is NZ$836
includes taxes & fees
1 June - 2 June
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
7.6 out of 10, Good, (4 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is NZ$380
includes taxes & fees
19 May - 20 May
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is NZ$919
includes taxes & fees
14 May - 15 May
Luxury 3BR Home Game Room Free Parking

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (13 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is NZ$604
includes taxes & fees
25 May - 26 May
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

THE OASIS @ LONG ISLAND

THE OASIS @ LONG ISLAND
Huntington Station
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
The price is NZ$810
includes taxes & fees
18 May - 19 May
THE OASIS @ LONG ISLAND

Luxury Prime 1BR Oasis in New York

Luxury Prime 1BR Oasis in New York
Bryn Mawr
The price is NZ$890
includes taxes & fees
18 May - 19 May
Luxury Prime 1BR Oasis in New York

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is NZ$522
includes taxes & fees
14 May - 15 May
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Walkable Townhouse with Garage & Yard, 45 min to NYC!

Walkable Townhouse with Garage & Yard, 45 min to NYC!
West Side
9.4 out of 10, Exceptional, (6 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is NZ$1,140
includes taxes & fees
18 May - 19 May
Walkable Townhouse with Garage & Yard, 45 min to NYC!

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is NZ$992
includes taxes & fees
18 May - 19 May
Spacious 3BR Luxe Escape near NYC

Family-Friendly Retreat w/ Trampoline & Grill

Family-Friendly Retreat w/ Trampoline & Grill
Locust Valley
The price is NZ$692
includes taxes & fees
17 May - 18 May
Family-Friendly Retreat w/ Trampoline & Grill
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Old Greenwich Hotel Reviews

Find out more about Old Greenwich

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 favorite 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 depends 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 NZ$226 per night. Entering your travel dates in the search wizard you might find 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. 

Frequently asked questions

Can I find holiday rentals in Old Greenwich?

Yes, there are holiday rentals close to the most popular sights in Old Greenwich, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Old Greenwich. Make sure you have time to check out the beaches and cafés during your trip.

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

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This holiday home rental outside of Old Greenwich is located next to a golf course, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as table football.

How many holiday rentals will I find in Old Greenwich?

Expedia has 12 holiday rentals for your stay in Old Greenwich.

What can I see and do in Old Greenwich?

Greenwich Point Park and Rosa Hartman Park are a couple of lovely local spots to get outside and enjoy nature. Commerce Park and Dundee Woods are other places to visit while you're in town.

What are holiday rentals like in Old Greenwich?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Old Greenwich. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family gatherings.