Old Greenwich Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Old Greenwich vacation rentals

Classic Suite | Iron/ironing board, free WiFi, bed sheets

Apartment in Fairfield Beach

DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (78 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Private kitchen

Apartment in Bryn Mawr

Luxury 1BR located in Prime Yonkers Area
2.0 star property
The price is ￥15,654
￥41,074 total
includes taxes & fees
Feb 8 - Feb 9
Luxury 1BR located in Prime Yonkers Area
Private kitchen

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is ￥15,819
￥41,664 total
includes taxes & fees
Jan 26 - Jan 27
Elegant Hideaway with Free Parking
Living area

Apartment in Bryn Mawr

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
The price is ￥17,401
￥43,038 total
includes taxes & fees
Jan 25 - Jan 26
Luxe 1BR Oasis - Prime NY Stay
Luxury House | Living area

Apartment in Southeast Yonkers

Spacious 3BR Luxe Escape near NYC
2.0 star property
The price is ￥31,466
￥50,856 total
includes taxes & fees
Feb 19 - Feb 20
Spacious 3BR Luxe Escape near NYC
Property grounds

Vacation Home in Greenwich

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
9.6 out of 10, Exceptional, (25 reviews)
"Very kind host very comfortable rooms"
United States
brendan o.
The price is ￥22,392
￥44,891 total
includes taxes & fees
Jan 23 - Jan 24
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Luxury House, Garden View | Dining

Apartment in Southeast Yonkers

Modern Comfort in the Heart of NYC
4.0 star property
The price is ￥71,154
￥99,999 total
includes taxes & fees
Feb 15 - Feb 16
Modern Comfort in the Heart of NYC
Living area

Apartment in Bryn Mawr

Uscale 2BR Escape in the Heart of NYC
2.0 star property
The price is ￥23,718
￥51,675 total
includes taxes & fees
Feb 8 - Feb 9
Uscale 2BR Escape in the Heart of NYC
Terrace/patio

Vacation Home in Southeast Yonkers

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
8.2 out of 10, Very Good, (18 reviews)
"Great place great location"
United States
Daquan H.
The price is ￥14,949
￥21,330 total
includes taxes & fees
Jan 26 - Jan 27
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Marina

Vacation Home in Cold Spring Harbor

Captain's Cottage - Cold Spring Harbor Water Views
10.0 out of 10, Exceptional, (74 reviews)
"Location was perfect!"
United States
Linda J P.
The price is ￥31,954
￥73,738 total
includes taxes & fees
Jan 21 - Jan 22
Captain's Cottage - Cold Spring Harbor Water Views
Apartment (1 Bedroom) | Interior

Apartment in Greenwich

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
The price is ￥36,684
￥63,874 total
includes taxes & fees
Jan 24 - Jan 25
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Dining

Vacation Home in Historic District

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
2.0 star property
10.0 out of 10, Exceptional, (9 reviews)
"Stayed with our adult children for a family wedding. Everyone enjoyed the spotless, attractive & appointed home with lovely king beds in all the rooms. It was a treat!Host was very attentive, would highly recommend!"
United States
Nancy B.
The price is ￥29,568
￥75,945 total
includes taxes & fees
Feb 5 - Feb 6
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Luxury Villa, Garden View | Dining

Villa in White Plains

Luxury NYC Home with Free Parking for 12
4.0 star property
The price is ￥71,154
￥107,550 total
includes taxes & fees
Feb 8 - Feb 9
Luxury NYC Home with Free Parking for 12
Living area

Apartment in Bryn Mawr

Luxury 3BR Family Home Game Room Parking
2.0 star property
The price is ￥31,466
￥58,763 total
includes taxes & fees
Feb 8 - Feb 9
Luxury 3BR Family Home Game Room Parking
Living area

Apartment in White Plains

Luxury 3BR Home Game Room Free Parking
2.0 star property
The price is ￥31,480
￥59,576 total
includes taxes & fees
Jan 21 - Jan 22
Luxury 3BR Home Game Room Free Parking
Private kitchen

Apartment in Downtown Stamford

Modern Luxury 1BR Stamford Getaway
10.0 out of 10, Exceptional, (1 review)
"The apartment is located in the hub bub of Stamford, a nice area very populated even in the evening where it feels safe. Apartment had all amenities that I needed. The host provided extra touches like a Keurig coffee pot stocked with Keurig cups and sugar. A washing machine and dryer were a plus as I like to pack only clean clothes. Bed was super comfortable. Modern design has a Zen vibe, great to decompress after travel. TV offered free movies that didn’t require my own subscription which...
United States
Debbie N.
The price is ￥26,090
￥49,610 total
includes taxes & fees
Feb 4 - Feb 5
Modern Luxury 1BR Stamford Getaway
Property grounds

Vacation Home in Waterside

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥24,915
￥52,065 total
includes taxes & fees
Jan 22 - Jan 23
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
1 bedroom, in-room safe, desk, free WiFi

Apartment in Hicksville

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
9.2 out of 10, Wonderful, (9 reviews)
"Nice location, clean and comfortable, and looking forward to possibly revisiting."
United States
Doug S.
The price is ￥15,812
￥26,477 total
includes taxes & fees
Feb 19 - Feb 20
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Coffee/tea maker, spices

Vacation Home in Huntington

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
10.0 out of 10, Exceptional, (5 reviews)
"Very clean, modern and comfortable. Host was helpful and a great communicator. We will definitely stay again! "
United States
Tricia H.
The price is ￥32,429
￥61,631 total
includes taxes & fees
Feb 1 - Feb 2
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Interior

Apartment in Northwest Yonkers

Cozy secret apartment with free parking in Yonkers
9.8 out of 10, Exceptional, (15 reviews)
"As described. Clean, responsive, great location, great communication. Staying again when avaliable!"
United States
Robert E.
The price is ￥19,765
￥46,177 total
includes taxes & fees
Feb 20 - Feb 21
Cozy secret apartment with free parking in Yonkers
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Old Greenwich Hotel Reviews

Hilton Garden Inn Westbury

Hilton Garden Inn Westbury

10/10 Excellent
"Great stay,room was very clean "
wayne 1-night trip
Posted 21 hours ago
Hilton Garden Inn Westbury

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 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?

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental near Old Greenwich is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Old Greenwich?

Expedia has 16 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.