Old Greenwich Holiday Rentals

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Holiday Rentals in Old Greenwich

The Mansion Hotel-style

2.5 star property
Norwalk
8.4 out of 10, Very good, (15)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is AU$223
includes taxes & fees
5 Dec - 6 Dec
The Mansion Hotel-style

DUNE Fairfield Beach

3.0 star property
Fairfield
9.0 out of 10, Wonderful, (76)
"Loved this venue! "
United States
adriano
DUNE Fairfield Beach

Guesthouse at Norwalk Inn

3.5 star property
Norwalk
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is AU$424
includes taxes & fees
21 Dec - 22 Dec
Guesthouse at Norwalk Inn

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

3.0 star property
Greenwich
The price is AU$354
includes taxes & fees
7 Dec - 8 Dec
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

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

Greenwich
9.6 out of 10, Exceptional, (21)
"Perfect place to rest. Excellent service! "
Mexico
Lucymar
The price is AU$390
includes taxes & fees
1 Dec - 2 Dec
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Piermont Oasis

Piermont
9.8 out of 10, Exceptional, (8)
"Carolyn was so amazing with her directions on how to park and check in. The apartment had everything as advertised. The ambiance was very private and peaceful. Walking distance to the town and pier. I would definitely stay again."
United States
Anonymous traveller
Piermont Oasis

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Hicksville
9.0 out of 10, Wonderful, (8)
"Had a great stay "
United States
Desiree
The price is AU$251
includes taxes & fees
8 Dec - 9 Dec
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

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 AU$751
includes taxes & fees
3 Dec - 4 Dec
Captain's Cottage - Cold Spring Harbor Water Views

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 AU$591
includes taxes & fees
12 Dec - 13 Dec
Modern Luxe 1BR Apt in Downtown Stamford

Cozy Apartment to Relax - Apartment "B"

2.0 star property
Getty Square
The price is AU$493
includes taxes & fees
3 Dec - 4 Dec
Cozy Apartment to Relax - Apartment "B"

Sweet Studio w/ Lounge & Pool Table

Westport
8.8 out of 10, Excellent, (6)
"So cute and comfortable "
United States
Maria
The price is AU$430
includes taxes & fees
1 Dec - 2 Dec
Sweet Studio w/ Lounge & Pool Table

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 AU$210
includes taxes & fees
29 Nov - 30 Nov
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

MasterRoom with in Suit Bathroom

Norwalk
The price is AU$203
includes taxes & fees
30 Nov - 1 Dec
MasterRoom with in Suit Bathroom

Gold Coast Getaway! Upscale Apt Near New Canaan

3.0 star property
Norwalk
The price is AU$317
includes taxes & fees
30 Nov - 1 Dec
Gold Coast Getaway! Upscale Apt Near New Canaan

2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

2.0 star property
Greenwich
The price is AU$352
includes taxes & fees
3 Dec - 4 Dec
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

Seabreeze at the beach west beach Stamford ct.

Cove - East Side - Shippan
9.8 out of 10, Exceptional, (9)
"Very comfortable and clean units. Outdoor area is great. Very nice neighborhood to walk around and right near a great bar. Appreciated the extras like beach towels, sunscreen, shampoo and laundry soap."
United States
Tom C.
The price is AU$579
includes taxes & fees
30 Nov - 1 Dec
Seabreeze at the beach west beach Stamford ct.

Gold Coast Getaway! Upscale Apt Near New Canaan

2.0 star property
Norwalk
The price is AU$322
includes taxes & fees
30 Nov - 1 Dec
Gold Coast Getaway! Upscale Apt Near New Canaan

New Modern Apartment

Bryn Mawr
10.0 out of 10, Exceptional, (5)
"great place to stay at absolutely comfortable and great neighborhood!"
United States
fransheska r.
The price is AU$436
includes taxes & fees
1 Dec - 2 Dec
New Modern Apartment

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

Waterside
10.0 out of 10, Exceptional, (8)
"Lovely little home in Stamford."
United States
Pat A.
The price is AU$516
includes taxes & fees
4 Dec - 5 Dec
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Luxe Provincial Style Studio w/ Patio & Parking

Huntington Station
10.0 out of 10, Exceptional, (2)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is AU$597
includes taxes & fees
2 Dec - 3 Dec
Luxe Provincial Style Studio w/ Patio & 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

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 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$210 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. 

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.