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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for Old Greenwich holiday rentals

Classic Suite | 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, (89 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is ฿6,250
฿9,180 total
includes taxes & fees
27 May - 28 May
DUNE Fairfield Beach
Luxury House | Living area

Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is ฿31,037
฿39,591 total
includes taxes & fees
25 May - 26 May
Two Wash
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is ฿31,037
฿39,436 total
includes taxes & fees
25 May - 26 May
Prime Luxe 3-BR NYC - Free Parking
Standard Room, 1 King Bed, Main Building | 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 ฿11,729
฿13,488 total
includes taxes & fees
25 May - 26 May
Guesthouse at Norwalk Inn
Luxury Apartment | 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 ฿32,671
฿41,255 total
includes taxes & fees
25 May - 26 May
3BR Prime Luxury NY - Free Parking
Villa, Smoking | 5 bedrooms

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is ฿27,438
฿46,876 total
includes taxes & fees
28 May - 29 May
Summer Pool Oasis Custom Bar Arcade Pool Table
Luxury Apartment | 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 ฿13,141
฿19,570 total
includes taxes & fees
25 May - 26 May
Luxury 3 BR Near NYC with Easy Parking
House | 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 ฿33,713
฿42,585 total
includes taxes & fees
26 May - 27 May
Modern Luxury Home w GameRoom & Parking
House, Pets allowed | 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 ฿16,634
฿23,478 total
includes taxes & fees
25 May - 26 May
3BR Prime Luxury near NYC w Arcade Room
Apartment (4 Bedrooms) | Interior

Easy NYC Access! Yonkers Apt 1/2 Mi to Metro-north

Easy NYC Access! Yonkers Apt 1/2 Mi to Metro-north
3.5 star property
Southeast Yonkers
The price is ฿17,969
฿36,758 total
includes taxes & fees
22 Jun - 23 Jun
Easy NYC Access! Yonkers Apt 1/2 Mi to Metro-north
Villa, Garden View | Living area

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 ฿17,969
฿25,420 total
includes taxes & fees
25 May - 26 May
Luxury NYC Home Game Room Free Parking
Luxury Duplex | 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 ฿11,402
฿17,951 total
includes taxes & fees
25 May - 26 May
Uscale 2BR Escape in the Heart of NYC
Luxury House | 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 ฿12,938
฿19,342 total
includes taxes & fees
25 May - 26 May
Spacious 3BR Luxe Escape near NYC
Luxury House, Garden View | 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 ฿11,402
฿17,624 total
includes taxes & fees
25 May - 26 May
Luxury 3BR Family Home Game Room Parking
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.6 out of 10, (119 reviews)
"Was a good Hotel friendly and clean"
United States
Tamara
The price is ฿4,861
฿5,591 total
includes taxes & fees
25 May - 26 May
Stamford Suites
Luxury Apartment | Living area

NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
4.4 out of 10, (5 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is ฿3,558
฿8,848 total
includes taxes & fees
25 May - 26 May
NY Luxury Apt Free Parking in PRIME Area
Luxury Apartment | Living area

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 ฿4,901
฿10,351 total
includes taxes & fees
25 May - 26 May
Luxury 1BR located in Prime Yonkers Area
Luxury Apartment, 1 Queen Bed with Sofa bed | Hypo-allergenic bedding, desk, laptop workspace, iron/ironing board

Global Luxury Suites White Plains

Global Luxury Suites White Plains
3.5 star property
White Plains
6.8 out of 10, (43 reviews)
"Please stay away from this horrible place!!! I have travelled all over the world but never dealt with such terrible company and their property. "
United States
Katerine
The price is ฿8,748
฿11,089 total
includes taxes & fees
26 May - 27 May
Global Luxury Suites White Plains
Luxury Villa, Patio | Living area

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 ฿21,236
฿28,626 total
includes taxes & fees
25 May - 26 May
Luxury 5 BR Home Free Parking
Apartment (1 Bedroom) | 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 ฿6,600
฿14,369 total
includes taxes & fees
26 May - 27 May
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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

East Norwich Inn

East Norwich Inn

8/10 Good
"Note there is no elevator so tricky for those mobility challenged. Good food options just across the road."
Jennifer 2-night trip
Posted less than an hour ago
East Norwich Inn

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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  • 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.

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.