Photo by Kate Persad

Old Greenwich Holiday Rentals

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Holiday Rentals in Old Greenwich

Charming Long Island Family Getaway with Pool. An hour from Hamptons

7.6 out of 10, Good, (7)
"Had a great time here. The house was clean and well maintained. The host communicated with us often and overall it was a great stay!"
The price is NZ$2,507
includes taxes & fees
11 Aug - 12 Aug
Charming Long Island Family Getaway with Pool. An hour from Hamptons

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

10.0 out of 10, Exceptional, (3)
"Great space! Very clean & well appointed! If you forgot to pack it, it is probably there!"
The price is NZ$777
includes taxes & fees
29 July - 30 July
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

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

The price is NZ$334
includes taxes & fees
20 July - 21 July
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 3-bedroom modern family retreat!

The price is NZ$819
includes taxes & fees
13 Aug - 14 Aug
Charming 3-bedroom modern family retreat!

Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

The price is NZ$4,083
includes taxes & fees
16 July - 17 July
Westport Dream Home 6 Bedroom / 5 Bathroom Pool and Jacuzzi Steps to town

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (4)
"Stayed with our adult children for a family wedding. Everyone enjoyed the spotless, attractive & appointed home with lovely king beds in all the rooms. It was a treat!Host was very attentive, would highly recommend!"
The price is NZ$1,009
includes taxes & fees
16 July - 17 July
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (62)
"Great home to stay. Beautiful area to explore!"
The price is NZ$1,097
includes taxes & fees
16 July - 17 July
Captain's Cottage - Cold Spring Harbor Water Views

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (20)
"Easy entrance and exit policy. Great communication from owners. Perfect location. "
The price is NZ$1,859
includes taxes & fees
6 Aug - 7 Aug
Waterview House Walking Distance from Cove Beach

Stylish Beach Home near Stamford Downtown/Beach

10.0 out of 10, Exceptional, (20)
"Everything was great"
The price is NZ$3,065
includes taxes & fees
2 Aug - 3 Aug
Stylish Beach Home near Stamford Downtown/Beach

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

9.0 out of 10, Wonderful, (2)
"the home was nice clean if in the area I would stay here again"
The price is NZ$927
includes taxes & fees
22 July - 23 July
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (21)
"Great home with fun ping pong table!"
The price is NZ$2,365
includes taxes & fees
17 July - 18 July
New Beach Home near Stamford Downtown/Shippan

The Luxury downtown. Pool Jim basketball

The price is NZ$431
includes taxes & fees
20 July - 21 July
The Luxury downtown. Pool Jim basketball

The Monroe | Elegant 2BR/2BA Downtown Stamford | Designed by Lavish & Live

The Monroe | Elegant 2BR/2BA Downtown Stamford | Designed by Lavish & Live

Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10.0 out of 10, Exceptional, (2)
"Lovely little home in Stamford."
The price is NZ$748
includes taxes & fees
31 July - 1 Aug
Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

9.2 out of 10, Wonderful, (5)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
The price is NZ$1,087
includes taxes & fees
18 July - 19 July
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

The West Lane Inn - Queen Room

9.4 out of 10, Exceptional, (3)
"Vert nice property, very nice and accommodating proprietor and staff."
The price is NZ$706
includes taxes & fees
17 July - 18 July
The West Lane Inn - Queen Room

Family Home near NY Beach, Private Workspace by Zen Living

10.0 out of 10, Exceptional, (5)
"Great getaway location. House was excellent, clean, and well put together. We had everything we needed and then some!"
The price is NZ$1,070
includes taxes & fees
20 July - 21 July
Family Home near NY Beach, Private Workspace by Zen Living

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

8.8 out of 10, Excellent, (6)
The price is NZ$427
includes taxes & fees
21 July - 22 July
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Family getaway.Commuter's Dream.Weddings&Events.Content House.Luxury Smart Home

10.0 out of 10, Exceptional, (1)
"Wow! I wish we could have stayed here more than just one night! The host was so accommodating of our last-minute reservation and provided friendly and thoughtful assistance throughout our stay. This home is stunning! Careful planning and top-of-the-line finishes clearly went into every detail of this beautiful family home and we were so comfortable in every space. Larchmont train station is just steps away and made our travel to NYC a breeze. The home truly has a park-like feel and the house is...
Family getaway.Commuter's Dream.Weddings&Events.Content House.Luxury Smart Home

Luxury 3Bed Private Apartment Near Manhattan

9.2 out of 10, Wonderful, (19)
"Host was very accommodating and easy to communicate with!"
The price is NZ$1,127
includes taxes & fees
22 July - 23 July
Luxury 3Bed Private Apartment Near Manhattan
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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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?

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

How many holiday rentals will I find in Old Greenwich?

Expedia has 16 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.