Old Greenwich Holiday Rentals

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Our top choices for Old Greenwich holiday rentals

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

The Mansion Hotel-style

The Mansion Hotel-style
2.5 star property
West Norwalk
8.2 out of 10, Very good, (21)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is NZ$256
includes taxes & fees
18 Dec - 19 Dec
The Mansion Hotel-style

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
9.2 out of 10, Wonderful, (9)
"Had a great stay "
United States
Desiree
The price is NZ$289
includes taxes & fees
13 Jan - 14 Jan 2026
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.4 out of 10, Very good, (40)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is NZ$544
includes taxes & fees
18 Dec - 19 Dec
Guesthouse at Norwalk Inn

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 NZ$476
includes taxes & fees
22 Dec - 23 Dec
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

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

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Greenwich
9.6 out of 10, Exceptional, (23)
"This was a great place! The host George and his wife were incredibly helpful and so nice, making the stay even better. I would absolutely recommend this spot to anyone and definitely plan to be back again!"
United States
Alexus C.
The price is NZ$507
includes taxes & fees
7 Jan - 8 Jan 2026
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
8.2 out of 10, Very good, (18)
"Great place great location"
United States
Daquan H.
The price is NZ$233
includes taxes & fees
20 Dec - 21 Dec
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is NZ$631
includes taxes & fees
29 Dec - 30 Dec
Modern Luxe 1BR Apt in Downtown Stamford

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, (9)
"Lovely little home in Stamford."
United States
Pat A.
The price is NZ$574
includes taxes & fees
19 Dec - 20 Dec
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (10)
"Easy check in; quick access to NYC. "
United States
Leah B.
The price is NZ$360
includes taxes & fees
17 Jan - 18 Jan 2026
Piermont Oasis

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
The price is NZ$556
includes taxes & fees
12 Jan - 13 Jan 2026
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 NZ$556
includes taxes & fees
12 Jan - 13 Jan 2026
Spacious 3BR Luxe Escape near NYC

45 Minutes from NYC, Entire House near Stamford Downtown,

45 Minutes from NYC, Entire House near Stamford Downtown,
Downtown Stamford
10.0 out of 10, Exceptional, (21)
"Our hosts were very attentive and responsive with communications. The house is lovely, clean, well stocked and in a great location. We thoroughly enjoyed our stay!"
United States
Megan P.
The price is NZ$727
includes taxes & fees
5 Jan - 6 Jan 2026
45 Minutes from NYC, Entire House near Stamford Downtown,

209 bedford

209 bedford
2.0 star property
Downtown Stamford
The price is NZ$353
includes taxes & fees
18 Dec - 19 Dec
209 bedford

Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (9)
"Excellent property, very clean, nicely furnished. One of the best VRBOs we have rented. Owner was exceptionally good about communication and went out of his way to make sure stay went well. Will come again. "
United States
David S.
The price is NZ$754
includes taxes & fees
2 Jan - 3 Jan 2026
Seabreeze at the beach west beach Stamford ct.

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, (73)
"Location was perfect!"
United States
Linda J P.
The price is NZ$830
includes taxes & fees
6 Jan - 7 Jan 2026
Captain's Cottage - Cold Spring Harbor Water Views

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7)
"So cute and comfortable "
United States
Maria
The price is NZ$480
includes taxes & fees
18 Dec - 19 Dec
Spacious Studio with Pool Table

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (7)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is NZ$640
includes taxes & fees
13 Jan - 14 Jan 2026
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (79)
"It was great"
United States
Natalie
The price is NZ$219
includes taxes & fees
18 Dec - 19 Dec
Stamford Suites

Gold Coast Getaway! Upscale Apt Near New Canaan

Gold Coast Getaway! Upscale Apt Near New Canaan
3.0 star property
West Norwalk
The price is NZ$614
includes taxes & fees
18 Dec - 19 Dec
Gold Coast Getaway! Upscale Apt Near New Canaan
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

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$219 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?

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside of 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.