Old Greenwich vacation rentals

We found 367 vacation rentals — enter your dates for availability

Discover a selection of 14 homes and other vacation rentals in Old Greenwich that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, vacation homes have the best amenities for hanging out with the people that matter most, which might include WiFi and a hot tub. You'll be able to choose a rental to meet everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Old Greenwich

Showing deals for:May 22 - May 29

Image gallery for ZENHOUSE Historic Sculptor Studio creator of Mount Rushmore mid century home

Modern mid century guest house. Built in 1955 inside of old court
10 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)

ZENHOUSE Historic Sculptor Studio creator of Mount Rushmore mid century home

Stamford

8% off
Price is $530
$3,711 for 7 nights
All fees included
ZENHOUSE Historic Sculptor Studio creator of Mount Rushmore mid century home

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Find out more about Old Greenwich

Why visit Old Greenwich

  • Family-friendly activities: Old Greenwich offers various attractions perfect for family outings, ensuring everyone has a great time.
  • Outdoor adventures: Enjoy beach activities and urban parks that provide ample opportunities for exploration and relaxation.
  • Charming neighborhoods: Discover nearby areas with a romantic vibe, adding to the unique coastal charm of Old Greenwich.
  • Scenic beauty: Experience the stunning landscapes that make Old Greenwich a perfect backdrop for a relaxing getaway.
  • Diverse accommodations: Choose from spacious apartments, cozy homes, and stylish condos to enhance your stay.

Popular types of accommodation in Old Greenwich

If you're exploring vacation rentals in Old Greenwich, you're in for a treat. Our most popular accommodation options include spacious apartments, cozy houses, and stylish condos. Whether you're looking for home rentals in Old Greenwich or convenient rentals near the area, we have a variety of choices to suit your needs. From CT apartments to comfortable bedroom apartments in Greenwich, you'll find the perfect place to unwind during your stay.

  • Apartments: The top choice for vacation rentals in Old Greenwich, offering convenient living spaces for solo travelers or families.
  • Houses: A great option for those seeking a home-like atmosphere, ideal for groups or families wanting to enjoy more privacy.
  • Condos: Perfect for visitors looking for modern amenities and a communal vibe, often located near attractions.
  • Cottages: These charming retreats provide a cozy and quaint experience, perfect for a romantic getaway.
  • Villas: A luxurious option, these spacious accommodations are ideal for travelers seeking comfort and style.**

Top attractions in and around Old Greenwich

Old Greenwich is perfect for family outings and outdoor adventures, offering a blend of beach activities, urban parks, and modern college campuses to explore. With a focus on cultural experiences and family-friendly attractions, visitors can enjoy a variety of activities that cater to their interests, making it an ideal destination for a memorable vacation.

  • Rye Playland: A classic amusement park located 7 miles from Old Greenwich, offering thrilling rides and family-friendly attractions. Enjoy a nostalgic atmosphere with outdoor adventures, games, and live entertainment that appeals to visitors of all ages.
  • Greenwich Avenue: Situated 3 miles from Old Greenwich, this vibrant street is known for its upscale shops, cafés, and restaurants, giving you a taste of city life. Stroll along and explore the local boutiques and dining options.
  • Greenwich Point Park: Nestled within Old Greenwich, this urban park features scenic views, walking trails, and picnic areas, making it ideal for families. Enjoy outdoor activities while soaking in the coastal beauty.

Things to do recommended for couples

For a romantic getaway in Old Greenwich, indulge in a relaxing treatment at Hand & Stone Massage and Facial Spa, just 3 miles away. Catch a show at Levitt Pavilion or Tarrytown Music Hall for an entertaining evening, both within a short drive. Enjoy your couple's retreat.

Things to do recommended for families

Families can have a blast at Chelsea Piers, just 3 miles away, with its vibrant sports atmosphere. For a more tranquil experience, visit Montgomery Pinetum and Waveny Park, both within 3 to 8 miles, offering serene spaces for relaxation and wellness.

Things to do recommended for groups

Groups visiting Old Greenwich can enjoy shopping and entertainment at Stamford Town Center, experience culture and romance at the Capitol Theatre, and embrace the outdoors with a round of golf at E. Gaynor Brennan Golf Course, all within a short drive from the town.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Old Greenwich

When planning your trip, whether you're traveling with a group, as a family, with pets, or seeking extended stays, be sure to prioritize your preferences in the search filters. Here are some helpful booking tips for Vrbo.

  • Traveling to Old Greenwich with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Old Greenwich with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with finding suitable amenities, like a private pool. Additionally, thinking about how close you are to family-friendly attractions is a smart move.
  • Taking your pets with you to Old Greenwich: For many families, a trip isn't truly fulfilled without their furry companion by their side. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that all family members feel comfortable and at home.
  • Planning for a long term stay visiting Old Greenwich: If you're searching for vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like parking, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay near Old Greenwich

Old Greenwich, Connecticut, offers a delightful blend of family-friendly activities and outdoor adventures, making it an ideal vacation spot. Visitors can explore the charming heart of Old Greenwich, enjoy nearby neighborhoods with a romantic vibe, and experience the welcoming atmosphere of the community. For those seeking a relaxing getaway, the area's scenic beauty and options for Glen Cove homes for rent provide the perfect backdrop for your stay. Discover the unique charm of this lovely coastal town.

  • Riverside: Located just 1 mile from Old Greenwich, Riverside is a charming city that offers a delightful blend of family-friendly and outdoor experiences. Visitors can enjoy leisurely days at the local beach and picturesque lake, engaging in various water activities or simply soaking up the sun. The vibrant shopping area and mall center provide ample opportunities for retail therapy, while the nearby theater showcases local performances and films. Riverside's welcoming atmosphere makes it an ideal spot for families looking to unwind and explore the outdoors.
  • Waterside: Also situated 1 mile from Old Greenwich, Waterside is a lively neighborhood known for its family-oriented and business-friendly environment. This area boasts a dynamic shopping scene and hosts a variety of entertainment options, including theaters and ski venues for winter enthusiasts. The neighborhood's modern square and tourist precinct are perfect for strolling, dining, or catching up with friends, making it a great destination for both leisure and business travelers. Waterside's unique blend of attractions ensures there's something for everyone to enjoy.
  • Stamford: Just 2 miles from Old Greenwich, Stamford is a bustling city that appeals to families and outdoor adventurers alike. The city features a diverse range of shopping areas and theaters, providing plenty of entertainment options for visitors. Educational attractions enhance the experience, making it a great spot for families looking to combine fun with learning. Stamford's modern square and tourist precinct are must-visit locations, where you can enjoy dining, shopping, and cultural experiences in a vibrant urban setting.

Best time to go to Old Greenwich

If you're planning a trip to Old Greenwich, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from May to July, while off-peak times, like October and December to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January32.0°F (0.0°C)Light RainMostly SunnySlightly LowSlightly Low
February33.3°F (0.7°C)Light RainMostly SunnyAverageSlightly Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageSlightly Low
April49.8°F (9.9°C)Light RainMostly SunnyAverageAverage
May59.7°F (15.4°C)Light RainMostly SunnySlightly HighAverage
June68.7°F (20.4°C)Light RainMostly SunnySlightly HighAverage
July75.7°F (24.3°C)Light RainMostly SunnySlightly HighSlightly High
August74.7°F (23.7°C)Light RainMostly SunnyAverageSlightly High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October57.9°F (14.4°C)Light RainMostly SunnySlightly LowAverage
November46.4°F (8.0°C)Light RainMostly SunnyAverageAverage
December38.5°F (3.6°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is simple

Are you interested in saving money on your upcoming adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even more savings. To discover a Vrbo property that aligns with your budget, simply use our filters to sort by price, location, and rental type. We're here to help you find the perfect getaway.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your complete booking. Being the planner definitely has its perks. When you enroll in our travel rewards program, One Key, you'll gain access to exclusive member discounts and earn OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient area to plan new adventures, manage your existing arrangements, or review your reservations. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To check out Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Friendly Old Greenwich will entice you

The beaches and other outdoor surroundings create an inviting atmosphere in Old Greenwich. This welcoming and romantic city entices travelers with its restaurants and shopping. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Old Greenwich

Are you hoping to discover things to do in the city? Venture out of your vacation home and check out everything that makes Old Greenwich a fun spot to vacation. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Chelsea Piers (3.3 mi / 5.4 km)
  • Rye Playland (6.9 mi / 11.1 km)
  • Bayville Adventure Park (8 mi / 12.9 km)
  • Norwalk Maritime Aquarium (9.4 mi / 15.1 km)
  • Glen Cove Municipal Golf Course (9.6 mi / 15.4 km)
  • Cold Spring Harbor Laboratory (12.3 mi / 19.9 km)

Exploring the natural landscape of Old Greenwich

Whether you're an active traveler or just want to take in the scenery, Old Greenwich is a great place to spend some time outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Greenwich Point Park (1.6 mi / 2.6 km)
  • West Beach (2.5 mi / 4 km)
  • Cove Island Park (3.7 mi / 6 km)
  • Houston Preserve (4.6 mi / 7.4 km)
  • Caumsett State Historic Park Preserve (8.7 mi / 14 km)
  • Planting Fields Arboretum State Historic Park (11.1 mi / 17.9 km)

Transportation options to and around Old Greenwich

Fly into Westchester County Airport (HPN), the closest airport, located 7.9 mi (12.7 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Farmingdale, NY (FRG-Republic), which is 21.6 mi (34.7 km) away.

Frequently asked questions

What is the best area to stay in Old Greenwich, Connecticut, United States of America when booking a vacation rental?
When considering a vacation rental in Old Greenwich, Connecticut, the area around the waterfront offers a charming and picturesque experience. This neighborhood is known for its proximity to beautiful beaches and stunning views of Long Island Sound. Visitors can enjoy the serene atmosphere while exploring local attractions like the picturesque Greenwich Point Park, which features lovely walking trails and sandy shores superb for relaxation or a picnic. Another highlight is the Old Greenwich Village, where you can discover quaint shops and delightful cafes, fostering a cozy community vibe.

In terms of vacation rentals, this area boasts a variety of properties, ranging from charming beach cottages to elegant homes, providing plenty of options to suit different preferences and budgets. Staying here gives you easy access to the scenic beauty of the waterfront while being close to the vibrant life of the village.
How much does it cost to rent a vacation home in Old Greenwich?
Prices for vacation rentals in Old Greenwich vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Old Greenwich to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Old Greenwich vacation house rentals?
You can find great discounts on house rentals in Old Greenwich on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Old Greenwich?
For renting a beach house in Old Greenwich, visitors should explore the scenic waterfront neighborhoods along Long Island Sound. The area around Greenwich Point Park is particularly appealing, offering beautiful views and access to sandy beaches. Many vacation rentals here feature amenities such as outdoor decks or patios for enjoying the coastal breezes, as well as fully equipped kitchens and spacious living areas, ideal for families or groups looking to spend time together.

Additionally, the neighborhoods near the Old Greenwich train station provide convenient access to both the beach and local shops and restaurants. Rentals in this area often come with modern comforts, like air conditioning and Wi-Fi, ensuring a relaxing stay. Some properties are also within walking distance of the picturesque Greenwich Harbor, where travelers can enjoy waterfront dining and boating activities.

The nearby Byram Park is another great option for beach house rentals, where families can enjoy picnics and playgrounds, making it a family-friendly location. Many properties here may include amenities such as outdoor grills and private yards, allowing guests to fully embrace the beach lifestyle.
What is the most popular type of vacation rental accomodation in Old Greenwich?
In Old Greenwich, vacation houses are the most popular type of rental, with several available throughout the area. These homes often feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces like gardens or decks that are superb for relaxation and gatherings. Many houses are situated in quiet, family-friendly neighborhoods, providing a peaceful atmosphere. Additionally, there are several apartments and mobile homes that cater to different preferences, offering amenities like cozy living areas and convenient access to local attractions.
Are there any family house rentals in Old Greenwich?
In Old Greenwich, Connecticut, there are several family-friendly house rentals available, making it an excellent choice for those traveling with kids. The area features charming homes with spacious living rooms, fully equipped kitchens for family meals, and outdoor patios ideal for relaxation or barbecues. Many properties are conveniently located near local parks, such as Binney Park, where families can enjoy playgrounds, walking trails, and picnic areas.

Additionally, the proximity to the beautiful beaches along Long Island Sound offers opportunities for swimming, beach games, and enjoying the seaside atmosphere. The local community is vibrant, with shops and dining options within easy reach, providing a blend of convenience and leisure.
Can I rent a vacation home with a pool or hot tub in Old Greenwich?
In Old Greenwich, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for travelers seeking relaxation and outdoor enjoyment. This charming coastal town offers a mix of amenities in its rentals, including private swimming pools, inviting hot tubs, and spacious outdoor areas superb for gatherings or family activities. Many properties also come equipped with fully stocked kitchens and comfortable living spaces, allowing guests to enjoy a home-like experience during their stay. Find your rental in Old Greenwich with a pool or a hot tub.
Can I find long-stay vacation rentals in Old Greenwich?
A long-stay vacation rental in Old Greenwich is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Old Greenwich?
In Old Greenwich, travelers can find several pet-friendly house rentals that cater to both comfort and convenience. Many of these homes are situated in picturesque neighborhoods, offering spacious layouts, modern kitchens, and outdoor spaces, great for families and pet owners alike. The area features beautiful parks such as Binney Park, which has walking trails and open green spaces where pets are welcome, providing an excellent environment for leisurely strolls and outdoor activities. Additionally, the nearby waterfront areas offer scenic views and opportunities for relaxation by the shore.
Are there any remote work vacation rentals in Old Greenwich?
In Old Greenwich, Connecticut, there are several vacation rentals suitable for remote work. This charming coastal town offers a variety of properties equipped with essential amenities for those needing to work while away. Many rentals feature high-speed internet and Wi-Fi access, ensuring a reliable connection for video calls and online tasks. Properties often include comfortable workspaces, such as dedicated desks or quiet nooks, making it easier to balance work and relaxation.

Additionally, travelers can enjoy the picturesque surroundings of Old Greenwich, with its beautiful beaches, parks, and local dining options nearby. The area is great for unwinding after a day of remote work, offering a blend of convenience and tranquility. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Old Greenwich vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Old Greenwich with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Old Greenwich?
In Old Greenwich, vacation rentals typically offer a range of appealing amenities. Travelers can expect most properties to include a fully equipped kitchen, allowing for convenient meal preparation. Many rentals also feature a deck or patio, providing a pleasant outdoor space to relax and enjoy the surroundings. For those traveling with pets, several options permit furry companions, ensuring a more inclusive experience. Additionally, many rentals come with a cozy fireplace, superb for creating a warm atmosphere during cooler months. Onsite parking is commonly available, making it easier for guests to explore the charming local area and nearby attractions.
When is the best time to visit Old Greenwich for a vacation rental?
The best time to visit Old Greenwich for a vacation rental is during the peak season from May to July, with July being particularly popular among travelers seeking a lively coastal experience. This period is ideal for enjoying the warm weather and engaging in outdoor activities such as beach outings, sailing, and exploring the charming local shops and restaurants along the picturesque waterfront.

During these summer months, temperatures typically range from the mid-70s to the low 80s Fahrenheit, providing a comfortable climate for sightseeing and leisurely strolls along the scenic beaches. The vibrant setting of Old Greenwich attracts families and groups looking to soak up the sun, making it a bustling yet enjoyable time to immerse yourself in the community's offerings.

For those considering a visit during the quieter months, January presents a less crowded option. While temperatures can dip to the low 30s Fahrenheit, this time allows for peaceful exploration of the town's winter charm and cozy indoor activities. You can enjoy a more intimate experience at local cafes or take leisurely walks along the shoreline, all while avoiding the peak tourist traffic.
How early should I book a Old Greenwich vacation rental?
Book your Old Greenwich vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Old Greenwich, Connecticut, United States of America?
In Old Greenwich, visitors can enjoy a blend of natural beauty and charming local attractions. A highlight is the scenic Greenwich Point Park, often referred to as Tod's Point, which offers beautiful beaches, walking trails, and stunning views of the Long Island Sound. The park is a superb spot for picnics and leisurely strolls along the shoreline.

The quaint downtown area features boutique shops and cozy cafes, providing a delightful experience for those looking to explore local flavors and unique finds. Nearby, the Bruce Museum offers insights into art, science, and natural history, making it a cultural focal point for visitors.

For outdoor enthusiasts, the nearby Byram Park offers recreational facilities, including a pool, playgrounds, and sports fields, contributing to a family-friendly atmosphere. Additionally, the Old Greenwich Yacht Club adds to the coastal charm, showcasing the area's maritime heritage and offering sailing opportunities.
Can I change or cancel my Old Greenwich home rental booking on Vrbo?
To find Old Greenwich vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Old Greenwich vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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