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Old Greenwich Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
6.2 out of 10, (184 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is P9,646
P11,093 total
includes taxes & fees
Sep 30 - Oct 1
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
The price is P20,554
P31,547 total
includes taxes & fees
Sep 30 - Oct 1
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
The price is P56,228
P71,932 total
includes taxes & fees
Sep 27 - Sep 28
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
The price is P30,925
P44,679 total
includes taxes & fees
Sep 27 - Sep 28
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
The price is P33,737
P46,883 total
includes taxes & fees
Sep 27 - Sep 28
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, (1 review)
"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
The price is P25,302
P39,364 total
includes taxes & fees
Sep 27 - Sep 28
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)
The price is P11,189
P22,107 total
includes taxes & fees
Sep 27 - Sep 28
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
The price is P22,429
P25,793 total
includes taxes & fees
Oct 4 - Oct 5
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
The price is P53,416
P69,068 total
includes taxes & fees
Sep 27 - Sep 28
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)
The price is P36,548
P50,197 total
includes taxes & fees
Sep 27 - Sep 28
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
The price is P37,485
P51,245 total
includes taxes & fees
Sep 27 - Sep 28
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
The price is P19,623
P31,262 total
includes taxes & fees
Sep 27 - Sep 28
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
The price is P11,085
P16,559 total
includes taxes & fees
Oct 5 - Oct 6
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
The price is P25,302
P37,616 total
includes taxes & fees
Oct 2 - Oct 3
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
The price is P22,616
P34,611 total
includes taxes & fees
Sep 30 - Oct 1
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
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
The price is P41,168
P77,051 total
includes taxes & fees
Sep 28 - Sep 29
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
The price is P19,623
P31,887 total
includes taxes & fees
Oct 2 - Oct 3
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
The price is P17,661
P29,067 total
includes taxes & fees
Oct 2 - Oct 3
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
The price is P20,186
P31,892 total
includes taxes & fees
Oct 4 - Oct 5
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

Amsterdam Hotel

Amsterdam Hotel

10/10 Excellent
"The hotel is good. It could use some updates. Everything works and it is clean."
Edward 1-night trip
Posted less than an hour ago
Amsterdam Hotel

Find out more about Old Greenwich

Search for holiday rentals in Old Greenwich on Expedia! You can easily find your home rentals, villas, holiday apartments in Old Greenwich using one of the methods below:

  • View our selection of featured holiday rentals in Old Greenwich
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Look no further and take a look at our great range of rental properties in Old Greenwich!

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.