Old Greenwich Holiday Rentals

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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Old Greenwich holiday rentals

Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (85 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is HK$1,401
HK$2,089 total
includes taxes & fees
10 May - 11 May
DUNE Fairfield Beach
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.6 out of 10, (113 reviews)
"Was very nice & clean. "
United States
Kelly
The price is HK$1,022
HK$1,175 total
includes taxes & fees
5 May - 6 May
Stamford Suites
Property entrance

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 HK$2,644
HK$3,040 total
includes taxes & fees
10 May - 11 May
Guesthouse at Norwalk Inn
Living area

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 HK$3,151
HK$4,693 total
includes taxes & fees
5 May - 6 May
Luxury 3 BR Near NYC with Easy Parking
Interior

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 HK$909
HK$2,671 total
includes taxes & fees
7 May - 8 May
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Living area

NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.0 out of 10, (4 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is HK$853
HK$2,122 total
includes taxes & fees
6 May - 7 May
NY Luxury Apt Free Parking in PRIME Area
Living area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
The price is HK$4,309
HK$6,096 total
includes taxes & fees
6 May - 7 May
Luxury NYC Home Game Room Free Parking
Living area

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is HK$2,734
HK$4,295 total
includes taxes & fees
6 May - 7 May
Luxury 3BR Home Game Room Free Parking
Living area

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
5.2 out of 10, (5 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is HK$1,175
HK$2,482 total
includes taxes & fees
5 May - 6 May
Luxury 1BR located in Prime Yonkers Area
Living area

3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (1 review)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveller
The price is HK$3,989
HK$5,630 total
includes taxes & fees
5 May - 6 May
3BR Prime Luxury near NYC w Arcade Room
Living area

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is HK$3,103
HK$4,638 total
includes taxes & fees
5 May - 6 May
Spacious 3BR Luxe Escape near NYC
Living area

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
8.0 out of 10, Very good, (1 review)
"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 HK$2,734
HK$4,305 total
includes taxes & fees
15 May - 16 May
Uscale 2BR Escape in the Heart of NYC
Living area

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
6.8 out of 10, (3 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is HK$2,734
HK$4,226 total
includes taxes & fees
5 May - 6 May
Luxury 3BR Family Home Game Room Parking
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is HK$7,443
HK$9,457 total
includes taxes & fees
6 May - 7 May
Prime Luxe 3-BR NYC - Free Parking
Interior

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
The price is HK$1,990
HK$6,193 total
includes taxes & fees
23 May - 24 May
3 Mi to Downtown: Spacious White Plains Home
Living area

Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is HK$7,443
HK$9,494 total
includes taxes & fees
5 May - 6 May
Two Wash
5 bedrooms

Westchester Summer Pool Pet Friendly Events Games

Westchester Summer Pool Pet Friendly Events Games
2.0 star property
Ossining
The price is HK$8,098
HK$12,932 total
includes taxes & fees
5 May - 6 May
Westchester Summer Pool Pet Friendly Events Games
In-room dining

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 HK$7,835
HK$9,893 total
includes taxes & fees
7 May - 8 May
3BR Prime Luxury NY - Free Parking
Living area

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
5.6 out of 10, (8 reviews)
"Property bedding was dirty, carpet dirty, sofas were dirty. Not was listed in the pictures. Asked me for $900 deposit through Zelle. No respond. Expedia needs to investigate this company for false advertising. "
United States
Liliana
The price is HK$8,085
HK$10,212 total
includes taxes & fees
5 May - 6 May
Modern Luxury Home w GameRoom & Parking
Dining

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 HK$3,526
HK$5,329 total
includes taxes & fees
6 May - 7 May
Luxury NYC Home with Free Parking for 12
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

LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

2/10 Terrible
"The walls are paper thin. The neighborhood is shady. The front desk is behind a bullet proof glass."
George 2-night trip
Posted 1 hour ago
LIV Hotel Bronx - Newly Built

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
  • Use the map to find apartments and other holiday homes in the Old Greenwich neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Old Greenwich while they last

Look no further and take a look at our great range of rental properties in Old Greenwich!

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?

Modern 5BR Home W/Private Backyard Basket Ball Hoop Near NY& Long Island Beaches: This holiday home rental outside of Old Greenwich offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Old Greenwich?

Expedia has 12 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.