256+ Private Villas and Holiday Rentals in Old Greenwich |
  1. USA
  2. Connecticut
  3. Stamford
  4. Old Greenwich

Old Greenwich Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Old Greenwich

Discover more than 256 vacation rentals available in Old Greenwich. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Old Greenwich.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Old Greenwich, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Old Greenwich. On average, places to stay near Old Greenwich offer 579.2 ft², with nightly prices averaging CA $615.

With Casai, finding and comparing holiday rentals in Old Greenwich is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

Show more
Show less

Top Accommodation Types in Old Greenwich

Type Count
Holiday Apartments 148
Vacation Homes 68
Cottages 4
Villas 2

Use these Quick Filters to Find a Holiday Rental in Old Greenwich

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Old Greenwich.

Weather in Old Greenwich, CT

View the weather forecast for Old Greenwich before booking your Old Greenwich Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Old Greenwich, CT

Casai offers a large selection of top attractions around Old Greenwich . Research things to do on your vacation before you visit Old Greenwich.


Greenwich Point Park
Bronx Zoo
Fordham University
New York Botanical Gardens
Capitol Theatre
Roosevelt Field Mall
Paramount Theater
Fairfield University
NYCB Theatre at Westbury
Empire City Casino
Westchester County Center
New Roc City
Purchase College
Norwalk Maritime Aquarium
Rye Playland
Ridgefield Playhouse
Oheka Castle
Van Cortlandt Park
Bronx Park
Farmingdale State College

Other Places to Stay in Old Greenwich, CT


Greenwich Point Park 99 Properties

Frequently Asked Questions About Old Greenwich?

What are the top holiday rentals in Old Greenwich?

With numerous options available in Old Greenwich, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Old Greenwich:

How many holiday rentals have private pools in Old Greenwich?

Discover a selection of holiday rentals with private pools near Old Greenwich with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Old Greenwich are best for families?

If you're searching for a family-friendly holiday home in Old Greenwich, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Old Greenwich:

How many Casai.ca holiday rentals are available in Old Greenwich?

As of 2025, Casai boasts over 256 properties listed in the Old Greenwich area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Old Greenwich.


People Also Ask

There are 256 Old Greenwich, CT Holiday Rentals

Recently Booked Holiday Rentals in Old Greenwich