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Holiday Rentals in Old Greenwich

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Holiday Rentals in Old Greenwich

MasterRoom with in Suit Bathroom

Norwalk
The price is €116
includes taxes & fees
15 Dec - 16 Dec
MasterRoom with in Suit Bathroom

Spacious 3BR Luxe Escape near NYC

2.0 star property
Southeast Yonkers
The price is €409
includes taxes & fees
16 Nov - 17 Nov
Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

2.0 star property
Southeast Yonkers
The price is €409
includes taxes & fees
16 Nov - 17 Nov
Spacious 3BR Luxe Escape near NYC

Nature Meets Village - Walkable Northport

Northport
The price is €620
includes taxes & fees
23 Nov - 24 Nov
Nature Meets Village - Walkable Northport

DUNE Fairfield Beach

3.0 star property
Fairfield
9.0 out of 10, Wonderful, (76)
"Great stay"
Canada
Gilles
DUNE Fairfield Beach

Guesthouse at Norwalk Inn

3.5 star property
Norwalk
8.4 out of 10, Very good, (39)
"Great space would be better if there were kuerig cups to go with the machine in the kitchen"
United States
Brian
The price is €276
includes taxes & fees
15 Dec - 16 Dec
Guesthouse at Norwalk Inn

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 €190
includes taxes & fees
16 Nov - 17 Nov
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor
10.0 out of 10, Exceptional, (71)
"Great home to stay. Beautiful area to explore!"
United States
Randy W.
The price is €415
includes taxes & fees
16 Nov - 17 Nov
Captain's Cottage - Cold Spring Harbor Water Views

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Hicksville
9.0 out of 10, Wonderful, (8)
"Nice location, clean and comfortable, and looking forward to possibly revisiting."
United States
Doug S.
The price is €144
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Gold Coast Getaway! Upscale Apt Near New Canaan

3.0 star property
Norwalk
The price is €180
includes taxes & fees
15 Dec - 16 Dec
Gold Coast Getaway! Upscale Apt Near New Canaan

Sweet Studio w/ Lounge & Pool Table

Westport
8.8 out of 10, Excellent, (6)
"This was our first time getting a VRBO while coming up for a family July 4th party. Everything was great. The space was clean and very comfortable and looked just like the pictures. It was only 5 minutes from our family’s house and very easy to find and in a nice neighborhood. The host was great and very easy to communicate with. "
United States
Annamarie W.
The price is €245
includes taxes & fees
15 Nov - 16 Nov
Sweet Studio w/ Lounge & Pool Table

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

Waterside
10.0 out of 10, Exceptional, (6)
"Exceptional space for our needs. We’d absolutely book again if the opportunity arises. Maritza was communicative and everything was easily accessible"
United States
Joanne
The price is €294
includes taxes & fees
17 Nov - 18 Nov
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Huntington
10.0 out of 10, Exceptional, (5)
"Ahead of my arrival the communication was timely and very detailed. The space was super clean, modern and open. Perfect studio for anyone traveling either alone, a couple or even a family with a baby - plenty of room for all the gear! Everything on ground level, close to town and convenient to the highway. I will definitely be back!!!"
United States
Karen E.
The price is €350
includes taxes & fees
15 Dec - 16 Dec
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Discover fun at NYC 30min drive stay at our cozy 2bed apartment in New Rochelle

New Rochelle
8.8 out of 10, Excellent, (19)
"I loved the home , it was clean, the host was on time with messages . Definitely worth the stay again"
United States
Keyara L.
The price is €344
includes taxes & fees
16 Nov - 17 Nov
Discover fun at NYC 30min drive stay at our cozy 2bed apartment in New Rochelle

Modern Luxe 1BR Apt in Downtown Stamford

Downtown Stamford
9.6 out of 10, Exceptional, (5)
"We had a great stay at this apartment! It was clean and the location couldn't be better. Communication with the host was easy and timely. I would definitely stay here again and recommend this place to friends/family visiting the Stamford area."
United States
Bobbie-Jo S.
The price is €334
includes taxes & fees
12 Dec - 13 Dec
Modern Luxe 1BR Apt in Downtown Stamford

Stylish Upscale Apt w/ Snack Bar & Sunny Deck

Huntington Station
10.0 out of 10, Exceptional, (10)
"It was a perfect place to stay. Clean, comfortable, everything I needed…"
United States
Thomas O.
The price is €334
includes taxes & fees
15 Nov - 16 Nov
Stylish Upscale Apt w/ Snack Bar & Sunny Deck

Luxe Provincial Style Studio w/ Patio & Parking

Huntington Station
10.0 out of 10, Exceptional, (2)
"This VRBO is ALL high end! The bath is over the top!!"
United States
Kevin
The price is €339
includes taxes & fees
15 Nov - 16 Nov
Luxe Provincial Style Studio w/ Patio & Parking

THE OASIS @ LONG ISLAND

Huntington Station
10.0 out of 10, Exceptional, (16)
"Couldnt ask for a better location "
United States
Erin A.
The price is €425
includes taxes & fees
16 Nov - 17 Nov
THE OASIS @ LONG ISLAND

Piermont Oasis

Piermont
9.8 out of 10, Exceptional, (6)
"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
The price is €185
includes taxes & fees
20 Nov - 21 Nov
Piermont Oasis

Seabreeze at the beach west beach Stamford ct.

Cove - East Side - Shippan
9.8 out of 10, Exceptional, (7)
"Very nice! Easy to work with and house was what we expected. "
United States
Jack P.
The price is €340
includes taxes & fees
16 Nov - 17 Nov
Seabreeze at the beach west beach Stamford ct.
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, apart-hotels, 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 €131 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.