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Old Greenwich Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Old Greenwich vacation rentals

Private kitchen
The Mansion Hotel-style

The Mansion Hotel-style

The Mansion Hotel-style
2.5 star property
West Norwalk
8.2 out of 10, Very Good, (22)
"Great service and very clean 👌 "
United States
JEAN
The price is P4,992
P5,741 total
includes taxes & fees
Dec 27 - Dec 28
The Mansion Hotel-style
Private beach nearby, sun loungers, beach umbrellas, beach towels
DUNE Fairfield Beach

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (78)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Private kitchen
JayZero

JayZero

JayZero
2.0 star property
Bryn Mawr
The price is P5,814
P15,256 total
includes taxes & fees
Jan 20 - Jan 21, 2026
JayZero
Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is P16,386
P18,844 total
includes taxes & fees
Dec 28 - Dec 29
Guesthouse at Norwalk Inn
Lobby
Stamford Suites

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (82)
"Everything was good other than the two options for breakfast and housekeeping entering the hotel room unannounced or no knocking"
United States
Laila
The price is P6,484
P7,457 total
includes taxes & fees
Dec 28 - Dec 29
Stamford Suites
Private kitchen
Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is P5,883
P15,494 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Elegant Hideaway with Free Parking
Living area
Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
The price is P6,461
P15,979 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Luxe 1BR Oasis - Prime NY Stay
Living area
Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
The price is P11,688
P18,890 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Spacious 3BR Luxe Escape near NYC
Private kitchen
Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
The price is P11,688
P18,890 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Spacious 3BR Luxe Escape near NYC
Interior
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is P7,048
P16,161 total
includes taxes & fees
Dec 30 - Dec 31
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Free WiFi
Two Wash

Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is P11,688
P21,827 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Two Wash
Free WiFi
Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is P11,688
P22,119 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Luxury 3BR Home Game Room Free Parking
Dining
Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
The price is P26,429
P39,949 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Luxury NYC Home with Free Parking for 12
Private kitchen
Luxury NY Home with Free Parking

Luxury NY Home with Free Parking

Luxury NY Home with Free Parking
4.0 star property
White Plains
8.0 out of 10, Very Good, (1)
"Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine. "
United States
Safiya
The price is P74,334
P90,843 total
includes taxes & fees
Dec 27 - Dec 28
Luxury NY Home with Free Parking
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 Old Greenwich Hotel Reviews

Hilton Garden Inn Westchester Dobbs Ferry, NY

Hilton Garden Inn Westchester Dobbs Ferry, NY

10/10 Excellent
"The room was clean and the staff at the reception was friendly and made the stay as seamless as possible."
Marion 1-night trip
Posted 2 days ago
Hilton Garden Inn Westchester Dobbs Ferry, NY

Find out more about Old Greenwich

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

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

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

Frequently asked questions

Can I find vacation rentals in Old Greenwich?

Yes, we offer vacation rentals close to well known points of interest in Old Greenwich, or you can go with a more remote option if you want a relaxing place to stay. Visitors like the top-notch restaurants and shops in Old Greenwich. Make sure you have time to check out the beaches and cafes during your trip.

What are some of the best vacation rentals in Old Greenwich?

3BR Prime Luxury near NYC w Arcade Room: Located near Old Greenwich, this vacation home rental is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals will I find in Old Greenwich?

Expedia has 16 vacation 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 vacation rentals like in Old Greenwich?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Old Greenwich. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip.