Greenwich vacation rentals

We found 914 vacation rentals — enter your dates for availability

Discover a selection of 18 homes and other vacation rentals in Greenwich that are perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll find the amenities you need and want, including air conditioning and WiFi. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Greenwich

Showing deals for:Jun 5 - Jun 12

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Front of house
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Fairfield Beach Modern Colonial

Fairfield

22% off
Price is $1,733
$12,128 for 7 nights
All fees included
Fairfield Beach Modern Colonial

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Find out more about Greenwich

Why visit Greenwich

  • Charming Downtown: Explore the vibrant atmosphere of downtown Greenwich, known for its luxury homes and local shops.
  • Beautiful Beaches: Enjoy the stunning coastal views and relaxing beach experiences along Greenwich's picturesque shoreline.
  • Urban Parks: Discover lush urban parks perfect for family outings, picnics, and outdoor activities.
  • Diverse Accommodations: Choose from a range of vacation rentals, from cozy homes to luxurious condos tailored to your needs.
  • Family-Friendly Activities: Engage in various family-oriented events and attractions, making it ideal for all ages.

Popular types of accommodation in Greenwich

Discover the perfect getaway with our vacation rentals in Greenwich. Choose from a variety of accommodations, including stylish apartments, charming houses, and luxurious condos. Whether you're seeking cozy home rentals or opulent Greenwich luxury homes for rent, we have options tailored to suit every traveler. Experience the beauty of Greenwich while enjoying the comfort and convenience of your ideal home away from home.

  • Apartments: The top choice for vacationers in Greenwich, offering modern conveniences and a home-like atmosphere.
  • Houses: A popular option for those seeking privacy and space, ideal for families or groups.
  • Condos: A stylish alternative that combines comfort and amenities, perfect for a relaxing getaway.
  • Cottages: Quaint and cozy, these rentals provide a charming retreat for a serene vacation experience.
  • Villas: Luxurious and spacious, villas offer an upscale experience for travelers looking for elegance.**

Top attractions in and around Greenwich

Greenwich, Connecticut, offers a delightful vacation for families and outdoor enthusiasts alike. With popular attractions such as urban parks, beautiful beaches, and modern colleges, visitors can enjoy a mix of culture and outdoor experiences. Whether you're exploring the local scenery or engaging in family-friendly activities, Greenwich is a perfect destination for those seeking a vibrant city getaway.

  • Rye Playland: A classic amusement park located 5 miles from Greenwich, Rye Playland offers a delightful experience for families with its thrilling rides, games, and beautiful waterfront views. The park's nostalgic charm makes it a perfect spot for outdoor adventures.
  • Greenwich Avenue: Situated in the heart of Greenwich, this vibrant street is lined with upscale shops, restaurants, and cafes, providing a lively urban atmosphere. It's a great place to stroll, dine, and soak in the local city vibes.
  • Westchester County Center: Just 8 miles away, this arts center hosts a variety of cultural events, including concerts, exhibitions, and performances. It’s a hub for arts enthusiasts and offers a rich cultural experience.

Things to do recommended for couples

For a romantic getaway in Greenwich, indulge in a relaxing treatment at Hand & Stone Massage and Facial Spa just 5 miles away. Enjoy an evening of live music at the Tarrytown Music Hall or Levitt Pavilion, both offering unique entertainment experiences, perfect for couples.

Things to do recommended for families

Your family will have a blast at Chelsea Piers, only 6 miles away, with its vibrant sports atmosphere. For some relaxation, head to Harbor Island Park, 8 miles from Greenwich, or explore the serene trails of Montgomery Pinetum, just 2 miles away, perfect for unwinding together.

Things to do recommended for groups

In Greenwich, your group can enjoy a captivating show at the Capitol Theatre, indulge in shopping and dining at The Westchester Mall, or hit the greens at Westchester Country Club for a fun day of golf and outdoor relaxation.

*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 Greenwich

If you're traveling with a group, family, pets, or planning for an extended stay, it's important to prioritize your preferences when filtering your options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Greenwich with a group: Think about how many bedrooms you require, along with features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Greenwich with young kids: Traveling with young kids can present some challenges. It’s important to prioritize their comfort and safety, along with providing age-appropriate amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Greenwich: For many families, a getaway wouldn’t feel complete without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Greenwich: If you're in search of vacation rentals offering 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 include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Greenwich

Greenwich, Connecticut, offers a delightful blend of family-friendly activities and romantic escapes. Explore the charming downtown Greenwich, renowned for its luxury homes and vibrant atmosphere. Nearby neighborhoods provide a welcoming vibe, perfect for relaxation and exploration. Immerse yourself in the idyllic Greenwich setting, where you can enjoy outdoor adventures and city-themed experiences, making it an ideal vacation spot for families, business travelers, or those seeking a romantic getaway.

  • Greenwich Municipal Center Historic District: The Greenwich Municipal Center Historic District is a vibrant area located in the heart of Greenwich. This neighborhood is a hub for family-friendly and outdoor activities, making it perfect for visitors of all ages. Travelers can enjoy a cultural experience by exploring local theaters and engaging in educational programs. The district is home to historic buildings that reflect its rich history, and modern educational institutions nearby offer a unique blend of old and new. With its charming shopping areas, you can easily spend a day exploring the historic district and enjoying its many attractions.
  • Strickland Road Historic District: Situated 2 miles from Greenwich, the Strickland Road Historic District is a picturesque village that invites families and couples to enjoy its outdoor charm. Renowned for its family beach and inviting esplanade, this area provides a wonderful destination for a romantic outing or a fun day with the kids. Visitors can venture to the local amusement park for thrilling rides or shop in the quaint stores that line the village streets. The warm, community-centric atmosphere makes it a delightful spot to relax and soak in the local culture.
  • Port Chester: Located 3 miles away from Greenwich, Port Chester is a lively village that offers a blend of family-oriented activities and cultural experiences. Visitors can immerse themselves in the local entertainment scene with theaters and shopping centers that cater to every taste. The historic buildings and tourist precinct reflect the village's vibrant past, while modern squares provide spaces for social gatherings and events. Whether you're looking to enjoy a night out or simply explore the local shops, Port Chester has something for everyone.

Best time to go to Greenwich

If you're planning a trip to Greenwich, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like November 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
April50.2°F (10.1°C)Light RainMostly SunnySlightly HighAverage
May60.1°F (15.6°C)Light RainMostly SunnyAverageAverage
June69.1°F (20.6°C)Light RainMostly SunnyAverageAverage
July76.1°F (24.5°C)Light RainMostly SunnySlightly HighSlightly High
August74.8°F (23.8°C)Light RainMostly SunnyAverageSlightly High
September68.4°F (20.2°C)Light RainMostly SunnySlightly HighAverage
October57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
November46.4°F (8.0°C)Light RainMostly SunnySlightly LowAverage
December38.5°F (3.6°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming journey? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your entire booking. Being the planner truly has its rewards. By enrolling in our travel rewards program, One Key, you'll gain access to exclusive member discounts and accumulate OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s user-friendly Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or organize your travel plans. You can easily access the properties you’ve saved or booked in the sections for Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

A haven for New Yorkers

From its upmarket shopping to its historic estates, Greenwich lives up to its reputation as one of the East Coast's most affluent towns. For decades, it has lured a constant stream of celebrities, investors and well-heeled New Yorkers. Greenwich sits in Fairfield County and is dotted with elegant hillside mansions, country clubs and a handful of sun-drenched beaches. The train ride from Grand Central takes just 40 minutes, which makes Greenwich vacation rentals eternally popular with New Yorkers in search of sun, sand and fresh air.

Sun-drenched days at Greenwich Point Park

Escape the rat race and head to Greenwich Point Park, an uninhabited peninsula fringed by beautiful sandy beaches. On a clear day, Tod's Point offers sweeping views of the distant NYC skyline. In summer, it's a great place to sign the kids up for a sailing lesson. Why not enjoy the New England high life as a family getaway, with a Greenwich vacation rental? From BBQs to Bloody Marys, a private sun deck will sweeten the deal. Take shelter from uncooperative weather at the Bush-Holley House Museum. Housed in an 18th-century cottage, it showcases a fantastic collection of American Impressionism.

Beachcombing and beautiful buildings in Greenwich

You won't want to make for the pearly beaches of the Connecticut coast until you've toured the handsome buildings of Old Greenwich. Joining a history walk that takes in all that and the Revolutionary War sights of Cos Cob is a great idea, while others will prefer to get their retail fix down the chic drag of Greenwich Avenue. Then it's time to hit the sands, unless – of course – you've managed to bag one of the coveted Greenwich vacation rentals that overlook the lapping Long Island Sound – then the sea's just on the doorstep…

Explore Greenwich's summer events calendar

Crowds peak in the summer, when Greenwich is brimming with locals and New Yorkers alike. Greenwich throws a lively summer events calendar, with outdoor concerts, farmers markets, Fourth of July fireworks and more. Fall brings clear skies, crisp temperatures are fiery foliage. It's too cold to swim but the weather is ideal for beach walks, brunches, shopping and golf. Winter can get chilly but it's a great excuse to rug up for a windswept walk on the beach or enjoy a cozy night by the fire.

Connect with nature in Long Island Sound

While it may tempt visitors with its boutiques and restaurants, Greenwich doesn't scrimp on nature. The town is fringed by 4 Long Island Sound beaches, including scenic Greenwich Point. With a long sandy beach, scenic walking trails and grassy picnic spots it's a great place to enjoy the sunshine. A handful of islands sit just offshore and serve as a haven for birdlife. Much of Great Captain's Island is occupied by a bird sanctuary, which is famous for its population of great blue herons.

Transportation to and around Greenwich

The nearest airport is in Westchester County Airport (HPN), located 4.9 mi (7.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into John F. Kennedy Intl. Airport (JFK), which is 27.6 mi (44.4 km) away.

Frequently asked questions

What is the best area to stay in Greenwich, Connecticut, United States of America when booking a vacation rental?
When looking for a great area to stay in Greenwich, Connecticut, one of the top neighborhoods to consider is the downtown area. This vibrant part of the town offers a charming mix of upscale boutiques, cafes, and restaurants, making it a superb spot for visitors who enjoy a lively option. One of the standout attractions here is the Bruce Museum, which showcases art and science exhibits in a beautifully designed space. Additionally, the nearby Greenwich Avenue is a delightful place to stroll and shop, featuring a variety of local and high-end brands.

Another excellent option is the waterfront neighborhood of Cos Cob. This picturesque area offers stunning views of the water and is home to the Cos Cob Harbor, which is a lovely spot for enjoying the outdoors. The nearby Greenwich Point Park is also a highlight, providing sandy beaches and scenic walking trails, ideal for families and nature enthusiasts alike.

In terms of vacation rentals, downtown Greenwich boasts a diverse range of options, from modern apartments to quaint historic homes, giving visitors plenty of choices to suit their preferences. Cos Cob, while more residential, also offers charming rental options that allow guests to enjoy a more relaxed atmosphere while still being close to the attractions of Greenwich.
How much does it cost to rent a vacation home in Greenwich?
Prices for vacation rentals in 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 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 Greenwich vacation house rentals?
You can find great discounts on house rentals in 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 Greenwich?
For renting a beach house in Greenwich, you'll want to explore the scenic waterfront areas, particularly along the Long Island Sound. The neighborhood of Old Greenwich is a prime spot, featuring charming beach houses that often come with amenities such as spacious decks, outdoor grills, and direct access to the sandy beaches. Many properties here offer stunning views of the coastline and are within walking distance to local parks and nature trails, making it superb for families and groups looking for a relaxing getaway.

Another excellent option is the area around Greenwich Point Park, where you can find beautifully maintained homes that typically include features like gourmet kitchens, private gardens, and sometimes even beach access with cabana facilities. This area is ideal for travelers wanting to enjoy outdoor activities, as it offers picnic areas, walking paths, and opportunities for swimming and water sports.

Additionally, the neighborhoods near the downtown area, like Byram, provide a mix of beach house rentals that are close to local shops, restaurants, and waterfront parks. Here, you can expect properties with modern amenities, including Wi-Fi, updated appliances, and comfortable living spaces, ideal for those looking to blend beach relaxation with urban conveniences.
What is the most popular type of vacation rental accomodation in Greenwich?
In Greenwich, vacation houses are the most popular type of rental, with about 18 available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, fully equipped kitchens, and often outdoor spaces such as gardens or patios, making them ideal for families or larger groups. Additionally, there are around 11 apartments available, which provide a more compact and convenient option for travelers. These apartments usually come with essential amenities like kitchens and cozy living spaces. For those seeking a more quaint experience, several condos and cottages are also offered, appealing to visitors looking for a unique stay.
Are there any family house rentals in Greenwich?
In Greenwich, Connecticut, families have a variety of rental options available, with around 14 properties to choose from. This affluent area is known for its beautiful neighborhoods, such as Old Greenwich and Riverside, both of which feature spacious houses that cater well to families. Many of these homes offer ample living space, fully equipped kitchens for preparing family meals, and outdoor areas superb for children to play or for hosting gatherings.

Visitors can enjoy proximity to local parks, like Greenwich Point Park, which boasts lovely beaches and picnic spots, making it ideal for family outings. Additionally, the town's vibrant downtown area offers shopping, dining, and cultural attractions.
Can I rent a vacation home with a pool or hot tub in Greenwich?
In Greenwich, Connecticut, there are several vacation homes available for rent that feature pools and hot tubs. This upscale coastal town offers a serene environment with beautiful neighborhoods like Belle Haven and Old Greenwich, where travelers can find well-appointed properties. Expect amenities such as private swimming pools, relaxing hot tubs, spacious outdoor patios, and fully equipped kitchens, ideal for both relaxation and entertaining.
Can I find long-stay vacation rentals in Greenwich?
A long-stay vacation rental in 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 Greenwich?
In Greenwich, there are several pet-friendly house rentals available, providing ample options for travelers with pets. Many of these properties are situated in picturesque neighborhoods, offering a mix of modern amenities and charming character. Expect to find vacation rentals featuring spacious backyards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups.

The waterfront areas of Greenwich, particularly near the Greenwich Point Park, offer beautiful views and easy access to outdoor spaces where pets can enjoy walks and playtime. Additionally, the nearby Bruce Museum and local parks provide enriching experiences for both pets and their owners, enhancing the overall stay in this beautiful coastal town.
Are there any remote work vacation rentals in Greenwich?
In Greenwich, Connecticut, there are numerous remote work-friendly vacation rentals available, with around 35 options throughout the area. These properties cater specifically to travelers seeking a productive environment while enjoying their stay. Many rentals come equipped with reliable internet access, dedicated workspaces featuring desks and chairs, and policies that support Wi-Fi usage, ensuring a comfortable and efficient remote working experience.

Travelers can expect a mix of amenities that enhance both work and relaxation, including spacious living areas, full kitchens for preparing meals, and outdoor spaces for unwinding after a workday. Additionally, the picturesque neighborhoods of Greenwich offer a variety of local parks and scenic spots, superb for taking breaks or enjoying nature. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Greenwich vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in 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 Greenwich?
In Greenwich, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals and enjoy the comforts of home. Many rentals feature a deck or patio, providing outdoor space for relaxation and enjoying the scenic surroundings. Onsite parking is commonly available, making it convenient for travelers with vehicles. Additionally, rentals often come with a coffee and tea maker for a warm beverage at any time, as well as blenders for those who enjoy smoothies or other blended drinks.
When is the best time to visit Greenwich for a vacation rental?
The best time to book a vacation rental in Greenwich is during the peak season from May to July, with July being particularly popular among travelers. This summer period is ideal for those looking to explore the charming coastal town, offering a vibrant setting filled with outdoor festivities, beautiful parks, and scenic views of Long Island Sound.

During these months, visitors can partake in a variety of activities, such as enjoying leisurely strolls along the waterfront or indulging in local dining experiences at outdoor cafes. The warm weather typically ranges from the mid-70s to low 80s Fahrenheit, providing comfortable conditions for sightseeing and outdoor adventures.

For travelers seeking a more budget-friendly experience, consider visiting in December. While this month marks the low season, it allows for a unique perspective on Greenwich, as the town is beautifully adorned for the holidays. Enjoy a peaceful ambiance, explore the local shops, and take in the festive decorations without the crowds.
How early should I book a Greenwich vacation rental?
Book your 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 Greenwich, Connecticut, United States of America?
In Greenwich, visitors can explore a range of attractions that highlight the town's rich history and natural beauty. The picturesque Greenwich Avenue is lined with upscale shops, restaurants, and cafes, making it a lovely area for leisurely strolls. Nearby, the Bruce Museum offers engaging exhibits on art and natural history, great for culture enthusiasts.

For outdoor lovers, Greenwich Point Park provides stunning views of Long Island Sound and sandy beaches, ideal for picnics and walks along the shore. The nearby Audubon Center at Greenwich is a fantastic spot for birdwatching and enjoying nature trails, showcasing the area's diverse wildlife.

Additionally, the historic Greenwich Village features charming architecture and a vibrant community atmosphere, where visitors can appreciate local art galleries and historic sites.
Can I change or cancel my Greenwich home rental booking on Vrbo?
To find 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 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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