Greenwich vacation rentals

We found 905 vacation rentals — enter your dates for availability

Discover a selection of 16 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:Mar 27 - Apr 3

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Exterior
10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Updated Farmhouse Retreat

Wilton

9% off
Price is $1,271
$8,900 for 7 nights
All fees included
Updated Farmhouse Retreat

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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 when booking a vacation rental?
When booking a vacation rental in Greenwich, Connecticut, one of the best areas to consider is the historic neighborhood of Old Greenwich. This charming area offers a picturesque coastal vibe, with beautiful beaches like Tod's Point, which is great for relaxing and enjoying the waterfront. Visitors can also explore the nearby Greenwich Point Park, a lovely spot for picnicking and hiking, providing breathtaking views of Long Island Sound.

Another excellent choice is the downtown Greenwich area, known for its vibrant atmosphere and accessibility to various shops, restaurants, and cultural attractions. Here, you can easily visit the Bruce Museum, which features art, science, and natural history exhibits. The lively ambiance of this neighborhood makes it a hub for both locals and visitors, with numerous vacation rental options available.

If you prefer a more tranquil setting, consider staying in the Cos Cob neighborhood. This area offers a quaint, small-town feel with local eateries and access to the scenic Cos Cob Harbor.
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, Connecticut, the area along the Long Island Sound is particularly appealing. The neighborhoods of Old Greenwich and Byram feature beautiful coastal properties that provide easy access to sandy beaches and picturesque waterfront views. In Old Greenwich, many vacation rentals offer amenities such as spacious decks, outdoor grills, and private beach access, ideal for families looking to make the most of their seaside getaway.

The Byram neighborhood also presents charming beach house options, often with features like modern kitchens, cozy living areas, and sometimes even private docks or kayaks for guests to enjoy the water. These rentals are conveniently located near local attractions such as the Byram Park, which includes picnic areas and playgrounds, making it an excellent choice for families.

Additionally, properties in these areas often come with convenient access to local restaurants and shops, providing a superb blend of relaxation and amenities. Find your rental near the beach in Greenwich.
What is the most popular type of vacation rental accomodation in Greenwich?
In Greenwich, vacation houses are the most popular type of rental accommodation, with about 15 available throughout the area. These homes provide ample space, often featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens, making them ideal for families or groups. Additionally, there are several apartments, condos, and cottages scattered across the town, particularly in neighborhoods close to the picturesque Greenwich Harbor and the lively downtown area. Most of these rentals offer comfortable living areas and convenient amenities, allowing travelers to enjoy a relaxing stay while exploring local attractions like the Bruce Museum and the scenic parks nearby.
Are there any family house rentals in Greenwich?
In Greenwich, Connecticut, there are several family-friendly house rentals available, with about 13 options to choose from. This charming town offers neighborhoods like Riverside and Cos Cob, where families can find spacious homes surrounded by beautiful landscapes. Many of these properties come with amenities such as fully equipped kitchens, large backyards for children to play, and cozy living areas great for family gatherings.

Visitors will appreciate the proximity to various attractions, including the scenic Bruce Park with its playgrounds and picnic areas, as well as the picturesque beaches along Long Island Sound. Additionally, local shops and restaurants are never far away, providing plenty of opportunities for family outings. See all family-friendly rentals in Greenwich.
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 come equipped with pools or hot tubs. This picturesque town offers a blend of coastal charm and suburban tranquility, making it a desirable destination for travelers. Rentals can be found in various neighborhoods, including the scenic waterfront areas along Long Island Sound and the more residential settings in Riverside and Old Greenwich.

Travelers can expect amenities such as private swimming pools, hot tubs, spacious outdoor decks, and well-appointed kitchens ideal for family gatherings or entertaining guests. Many properties also feature beautifully landscaped gardens and outdoor dining spaces, great for enjoying the serene surroundings. Find your rental in Greenwich with a pool or a hot tub.
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, offering a range of amenities to accommodate travelers and their furry companions. Many of these homes are located in picturesque neighborhoods, providing easy access to parks and outdoor spaces. Expect to find properties featuring spacious backyards, modern kitchens, and comfortable living areas, making them great for families or groups.

The area is known for its beautiful parks, such as Bruce Park and Greenwich Point Park, where pets can enjoy walking trails and open spaces. These parks also provide scenic waterfront views and picnic areas, enhancing the outdoor experience for both pets and their owners. Additionally, some vacation rentals may include amenities like pet-friendly furnishings, fenced yards, and proximity to pet-friendly cafes and shops, ensuring a pleasant stay for all guests. See all pet-friendly rentals in Greenwich.
Are there any remote work vacation rentals in Greenwich?
In Greenwich, Connecticut, there are numerous remote work vacation rentals available, with around 26 options to choose from. This affluent area offers a blend of suburban charm and proximity to New York City, making it an ideal location for remote workers. Many properties feature essential amenities such as high-speed Wi-Fi, dedicated office spaces with desks and ergonomic chairs, and additional conveniences like computer monitors and safes for added security.

Travelers can expect a comfortable and productive environment, supported by spacious living areas that may also include outdoor spaces for relaxation after work hours. The scenic neighborhoods of Greenwich, with their tree-lined streets and historic architecture, provide a pleasant backdrop, while nearby parks and recreational areas offer opportunities for outdoor activities. 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 typically include WiFi, allowing guests to stay connected during their stay. Most rentals feature fully equipped kitchens, which often come with essential appliances like coffee and tea makers, blenders, and kitchen islands for added convenience and space while cooking.
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?
In Greenwich, visitors can explore a variety of attractions that highlight the area's natural beauty and cultural heritage. The Greenwich Avenue area features upscale shops, boutiques, and restaurants, making it a vibrant hub for dining and shopping. Nearby, guests can visit the Bruce Museum, which showcases art and natural history exhibits.

For outdoor enthusiasts, the picturesque Greenwich Point Park offers scenic views of Long Island Sound and walking trails, superb for leisurely strolls or picnics. The Byram Park area features recreational facilities and a beach, ideal for families looking to enjoy the waterfront.
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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