A calm lake with reflections of trees and a stone structure on the right.

Old Greenwich Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Old Greenwich vacation rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (185 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$159 nightly
The price is $183
Oct 12 - Oct 13
Total with taxes and fees
Stamford Suites
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

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

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
$439 nightly
The price is $505
Oct 9 - Oct 10
Total with taxes and fees
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A breakfast buffet with pastries, fruits, and a coffee station.

3. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
$1,134 nightly
The price is $1,263
Oct 2 - Oct 3
Total with taxes and fees
3BR Prime Luxury NY - Free Parking
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

4. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
$680 nightly
The price is $778
Oct 2 - Oct 3
Total with taxes and fees
Luxury NYC Home Game Room Free Parking
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

5. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
$1,084 nightly
The price is $1,207
Oct 2 - Oct 3
Total with taxes and fees
Prime Luxe 3-BR NYC - Free Parking
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

6. Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, (2 reviews)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
$611 nightly
The price is $680
Oct 2 - Oct 3
Total with taxes and fees
Luxury NYC Home with Free Parking for 12
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

7. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, (1 review)
$329 nightly
The price is $377
Oct 2 - Oct 3
Total with taxes and fees
Elegant Hideaway with Free Parking
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

8. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
$294 nightly
The price is $339
Oct 5 - Oct 6
Total with taxes and fees
Guesthouse at Norwalk Inn
A modern living room with a sofa, armchairs, a coffee table, and a dining area with a table and chairs.

9. Two Wash

Two Wash
2.0 star property
Bryn Mawr
$1,083 nightly
The price is $1,212
Oct 2 - Oct 3
Total with taxes and fees
Two Wash
A modern living room with a sofa, armchairs, and a glass coffee table.

10. Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking
2.0 star property
Bryn Mawr
2.0 out of 10, (1 review)
$783 nightly
The price is $876
Oct 2 - Oct 3
Total with taxes and fees
Luxury 5 BR Home Free Parking
A modern living room with a white sofa, a glass coffee table, and a marble-patterned rug.

11. Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
5.0 out of 10, (12 reviews)
"Though the privous occupants refused to vacate the property in time but the landlord was suupportive went out of their way and provided a refund option and an alternative...we took the alternative which happen to be better than the originally booked property ... Will use this management and property owner in our upcoming short terms rentals....."
United States
abdelwahab
$1,347 nightly
The price is $1,507
Oct 5 - Oct 6
Total with taxes and fees
Modern Luxury Home w GameRoom & Parking
A modern living room with a stone wall, a flat-screen TV, a white sofa, and a kitchen area with a bar counter and chairs.

12. Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
2.0 out of 10, (2 reviews)
"My experience did not match the listing. I was asked to make payment outside the platform and the check-in process was not clear. I would not recommend this property. ⸻ ⭐⭐ Balanced Review The property did not meet expectations. When I arrived, the check-in process was unclear and the home appeared to be partially occupied. I was also instructed to make a payment outside of Hotels.com instead of using the platform. This caused confusion and concern. I would suggest the listing be...
United States
Dianelly
$482 nightly
The price is $539
Oct 2 - Oct 3
Total with taxes and fees
Luxe 1BR Oasis - Prime NY Stay
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

13. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (113 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
$235 nightly
The price is $270
Oct 7 - Oct 8
Total with taxes and fees
DUNE Fairfield Beach
A living room with a sectional sofa, a white armchair, a patterned rug, and a wooden floor.

14. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
7.0 out of 10, Good, (4 reviews)
"My family and I were satisfy with the stay I’ll definitely coming back"
United States
Josephine
$583 nightly
The price is $652
Oct 2 - Oct 3
Total with taxes and fees
Spacious 3BR Luxe Escape near NYC
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

15. Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
$535 nightly
The price is $599
Oct 2 - Oct 3
Total with taxes and fees
Luxury 3 BR Near NYC with Easy Parking
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

16. Nyc-area Escape Near River, Trails & Mta!

Nyc-area Escape Near River, Trails & Mta!
3.0 star property
Ossining
$748 nightly
The price is $833
Oct 21 - Oct 22
Total with taxes and fees
Nyc-area Escape Near River, Trails & Mta!
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

17. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
$1,107 nightly
The price is $1,233
Oct 5 - Oct 6
Total with taxes and fees
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

18. Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
9.0 out of 10, Wonderful, (2 reviews)
"The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays."
United States
Adj Fatou
$491 nightly
The price is $549
Oct 2 - Oct 3
Total with taxes and fees
Uscale 2BR Escape in the Heart of NYC
A modern living room with a beige sectional sofa, a green armchair, a marble-patterned rug, a gold coffee table, and a flat-screen TV mounted on a white wall.

19. Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
4.8 out of 10, (5 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
$482 nightly
The price is $539
Oct 2 - Oct 3
Total with taxes and fees
Luxury 3BR Family Home Game Room Parking
A modern kitchen with white cabinets, a central island with stools, a stone accent wall, a flat-screen TV, and a beige sofa with teal cushions.

20. Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
4.8 out of 10, (6 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
$492 nightly
The price is $551
Oct 2 - Oct 3
Total with taxes and fees
Luxury 1BR located in Prime Yonkers Area
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 Westbury

Hilton Garden Inn Westbury

10/10 Excellent
"Muy limpio, todo nuevo, ellos ya no tenían el tipo de habitación que reservamos así es que nos hicieron un upgrade gratuito. Excelente servicio, la comida del bar excelente, buenos precios, sirven mucho y el bar tender dio un excelente servicio. Definitivamente regresaré."
JEANCARLOS 2-night trip
Posted 1 hour ago
Hilton Garden Inn Westbury

Find out more about Old Greenwich

Everything you need to know about Old Greenwich vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Old Greenwich vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Old Greenwich vacation 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 low season months. For more hustle and bustle, you may prefer to visit Old Greenwich in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $183 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Old Greenwich rentals

At Expedia, we put the best Old Greenwich vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Modern Luxury Home w GameRoom & Parking: Located near Old Greenwich, this vacation home rental is situated near the airport and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Old Greenwich?

Expedia has 13 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.