Greenwich holiday lettings

We found 874 holiday rentals — enter your dates for availability

Discover a selection of 15 homes and other holiday rentals in Greenwich that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include parking and a washer and dryer. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Greenwich

Showing deals for:6 Mar - 13 Mar

Image gallery for Updated Farmhouse Retreat

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

Updated Farmhouse Retreat

Wilton, CT

8% off
Price is £7,621
for 7 nights, 1 room
£1,089 per night
includes taxes & fees
Updated Farmhouse Retreat

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Greenwich

  • Scenic Beaches: Enjoy the tranquil beaches of Old Greenwich, perfect for relaxation and family outings.
  • Charming Urban Parks: Explore numerous parks that offer lush landscapes and outdoor activities for all ages.
  • Cultural Experiences: Immerse yourself in the local culture with vibrant cafés and friendly locals enhancing your visit.
  • Diverse Accommodation: Choose from a range of charming apartments and modern condos, catering to every preference.
  • Family-Friendly Activities: Engage in various family-oriented attractions that make Greenwich an ideal holiday destination.

Popular types of accommodation in Greenwich

Planning a getaway to Greenwich? The next step is selecting the perfect accommodation. From charming apartments and houses to modern condos, you’ll find a variety of rentals to suit your needs. Whether you’re seeking rentals with outdoor seating for al fresco dining or properties with beach access, Greenwich has something for everyone. Explore your options and enjoy a delightful stay in this historic area!

  • Apartments: The most sought-after option for holiday rentals in Greenwich, ideal for those seeking comfort and convenience.
  • Houses: A popular choice for families and groups, offering spacious living and a home-like atmosphere.
  • Condos: A well-liked alternative, providing modern amenities and often situated in vibrant communities.
  • Cottages: Charming and cosy, these rentals are perfect for a quaint getaway in a picturesque setting.
  • Villas: Luxurious options for those looking to indulge, often featuring stunning views and ample space.**

Top attractions in and around Greenwich

Greenwich, Connecticut, is an excellent destination for family outings and outdoor adventures. With its urban parks, beautiful beaches, and modern universities, there is plenty to explore. The area's attractions cater to those seeking cultural experiences, family-friendly activities, and opportunities to enjoy the great outdoors. Whether you’re visiting with loved ones or solo, Greenwich offers a delightful mix of urban and natural delights for every traveller.

  • Greenwich Avenue: Experience the vibrant atmosphere of Greenwich Avenue, a lively street brimming with boutique shops, cafes, and restaurants, perfect for a leisurely stroll and people-watching.
  • Rye Playland: Just 3.1km away, this classic amusement park offers thrilling rides and family-friendly attractions, making it an ideal destination for outdoor fun and adventure with loved ones.
  • Westchester County Center: Located 5.0km from Greenwich, this cultural hub hosts various events, from art exhibitions to live performances, immersing you in the local arts scene.

Things to do recommended for couples

Planning a romantic getaway in Greenwich? Indulge in the soothing treatments at Hand & Stone Massage and Facial Spa, or enjoy a concert at Tarrytown Music Hall. For a lovely evening, head to Levitt Pavilion for delightful live music under the stars.

Things to do recommended for families

Families will have a fantastic time at Chelsea Piers, indulging in various sports activities. For a leisurely day, head to Harbor Island Park, perfect for relaxation. Don't miss the adventure at Legoland Discovery Center Westchester, where kids can enjoy interactive fun and creativity.

Things to do recommended for groups

Enjoy a night out at the Capitol Theatre, merely 1.9km from Greenwich, or indulge in retail therapy at The Westchester Mall, 4.3km away. For some outdoor fun, swing by the Westchester Country Club, just 2.5km away, for a round of golf with friends.

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

If you're travelling with a group, family, pets, or planning an extended stay, it's important to apply the right filters to meet your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Greenwich with a group: Think about how many bedrooms you'll require, as well as any additional features like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Greenwich with young kids: Travelling with young children can present its difficulties. It’s important to prioritise their comfort and safety, along with suitable facilities, like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are friendly for families.
  • Taking your pets with you to Greenwich: For many families, a holiday isn't truly fulfilling without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Greenwich: If you're in search of holiday 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 accommodations. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in and around Greenwich

Greenwich, Connecticut, offers a delightful blend of family-friendly activities and picturesque outdoor settings. Visitors can explore charming areas like Old Greenwich, with its inviting beaches and serene town beaches perfect for relaxation. The vibrant atmosphere and friendly locals make it an ideal spot for a romantic getaway or a leisurely family holiday. Enjoy outdoor seating at local cafés while soaking in the beautiful surroundings and experiencing the unique vibes of this lovely town.

  • Greenwich Municipal Center Historic District: The Greenwich Municipal Center Historic District is a charming neighbourhood brimming with cultural heritage. Nestled in the heart of Greenwich, this district offers a delightful combination of family-friendly activities and outdoor experiences. Visitors can enjoy theatre performances and various events at the arena entertainment facility, while the shopping areas provide ample opportunities for retail therapy. Notable local landmarks include historic buildings and a picturesque tourist precinct, perfect for leisurely strolls and taking in the scenic highland views.
  • Strickland Road Historic District: Situated a mere 1.2km from Greenwich, the Strickland Road Historic District is a quaint village ideal for families and couples seeking a romantic getaway. The area features an amusement park that promises fun for all ages, alongside charming shopping options. Visitors will appreciate the inviting town neighbourhood atmosphere, and the proximity to a family beach and esplanade makes it an excellent spot for outdoor activities and relaxation by the water.
  • Port Chester: Located 1.9km away from Greenwich, Port Chester is a vibrant village known for its rich cultural scene and entertainment offerings. Families will find plenty to do here, with theatres hosting live performances and a variety of shopping areas, including a bustling shopping centre. The local landmarks such as historic buildings and a modern square add to the appeal, making Port Chester an exciting destination for those looking to immerse themselves in local culture and enjoy a lively atmosphere.

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 keen to save on your upcoming getaway? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, you may find substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a user-friendly area for you to plan new journeys, continue from where you last stopped, or manage your travel arrangements. You can easily find your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Why people love visiting charming Greenwich

Enjoy the churches and other features of Greenwich. This romantic city is known for its boating, cheese shops and restaurants. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Greenwich

Are you hoping to discover attractions to see while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Greenwich a fun place to get away to. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Rye Playland (4.8 mi / 7.7 km)
  • Hand & Stone Massage and Facial Spa (5.1 mi / 8.2 km)
  • Chelsea Piers (6.2 mi / 10 km)
  • Stanwich Club (6.9 mi / 11.1 km)
  • Bayville Adventure Park (8.5 mi / 13.7 km)
  • Norwalk Maritime Aquarium (12.2 mi / 19.6 km)

Exploring the natural landscape of Greenwich

Whether you're an active traveller or just want to appreciate the scenery, Greenwich is a great place to get out in nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Greenwich Point Park (2.9 mi / 4.6 km)
  • West Beach (5.6 mi / 9 km)
  • Cove Island Park (6.8 mi / 11 km)
  • Caumsett State Historic Park Preserve (11 mi / 17.8 km)
  • Planting Fields Arboretum State Historic Park (11.9 mi / 19.2 km)
  • Sands Point Preserve (12.1 mi / 19.4 km)

Transport to and around Greenwich

The nearest airport is in White Plains, NY (HPN-Westchester County), located 4.9 mi (7.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into LaGuardia Airport (LGA), which is 21.6 mi (34.7 km) away.

Frequently asked questions

What is the best area to stay in Greenwich when booking a holiday rental?
When considering a holiday rental in Greenwich, Connecticut, the Old Greenwich neighbourhood is an excellent choice. This charming coastal area offers a delightful mix of beachside relaxation and vibrant community life. Visitors can enjoy the scenic beauty of the nearby Greenwich Point Park, which features stunning views of Long Island Sound and lovely sandy beaches. The area is also home to the quaint shops and cafés along Sound Beach Avenue, where you can savour local delicacies and explore unique boutiques.

Another appealing option is the Greenwich Avenue area, known for its upscale shopping and dining experiences. This lively stretch is lined with a variety of shops, from high-end fashion boutiques to artisanal food markets. The historic Greenwich Historical Society is also nearby, providing a fascinating glimpse into the region's rich heritage.
How much does it cost to rent a holiday home in Greenwich?
Prices for holiday 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 holiday 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 around Tod's Point is highly recommended. This picturesque coastal region offers beautiful waterfront properties with easy access to sandy beaches and stunning views of Long Island Sound. Many rentals in this vicinity come equipped with modern amenities such as outdoor decks, BBQ grills, and spacious living areas, making them great for families or groups looking to enjoy a relaxing beach holiday.

Additionally, the neighbourhood of Old Greenwich is another excellent option, where you can find charming beach houses that often include private gardens and proximity to local shops and restaurants. Properties here may feature amenities like outdoor showers, beach gear storage, and well-appointed kitchens, allowing for a comfortable stay while enjoying the coastal lifestyle.
What is the most popular type of holiday rental accomodation in Greenwich?
In Greenwich, holiday houses are the most popular rental option, with around 17 available throughout the area. These houses typically offer spacious living arrangements, multiple bedrooms, and amenities such as fully equipped kitchens and outdoor spaces for relaxation. Many are situated in picturesque neighbourhoods, providing a serene environment while still being close to local attractions. Additionally, there are several apartments, condos, and cottages available, suiting different preferences and group sizes.
Are there any family house rentals in Greenwich?
In Greenwich, Connecticut, there are numerous family-friendly house rentals available, with around 13 options for visitors to consider. This charming town offers a delightful blend of suburban tranquillity and proximity to urban attractions, making it an excellent choice for families. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and private outdoor spaces where children can play and explore.

Travellers can find homes in neighbourhoods like Riverside and Cos Cob, both of which are known for their welcoming atmospheres and access to local parks. The picturesque Riverside Park, with its waterfront views and playgrounds, is great for outdoor activities, while Cos Cob offers a quaint village feel with shops and eateries.
Can I rent a holiday home with a pool or hot tub in Greenwich?
In Greenwich, Connecticut, there are several holiday homes available for rent that feature pools and hot tubs. This affluent town offers a mix of charming residential areas and scenic waterfront views, making it an attractive destination for travellers seeking relaxation and leisure. Many of the properties come equipped with private pools, expansive outdoor spaces, and hot tubs, superb for unwinding after a day of exploring the local attractions. Expect amenities such as fully equipped kitchens for home-cooked meals, spacious living areas, and outdoor patios ideal for gatherings.
Can I find long-stay holiday rentals in Greenwich?
A long-stay holiday rental in Greenwich is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Greenwich?
In Greenwich, Connecticut, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with furry companions. These holiday homes often feature amenities such as spacious backyards, modern kitchens, and cosy living areas, making them ideal for families or groups. Many properties are designed with comfort in mind, showcasing features like outdoor patios and fireplaces for those cooler evenings.

The neighbourhood of Old Greenwich, known for its quaint charm, offers proximity to parks and the scenic waterfront, allowing for enjoyable walks with pets. Nearby, the Greenwich Point Park provides expansive green spaces and beach access, great for exploring with your four-legged friend. Another appealing area is Riverside, which features lovely tree-lined streets and local parks that are dog-friendly, ensuring plenty of opportunities for outdoor activities.
Are there any remote work holiday rentals in Greenwich?
In Greenwich, Connecticut, there are a variety of remote work holiday rentals available, with around 26 options to choose from. This affluent area, known for its picturesque landscapes and vibrant community, offers properties that cater to the needs of remote workers. Many rentals come equipped with dedicated office spaces, including desks and comfortable desk chairs, allowing for a productive work environment. Additional amenities often include high-speed Wi-Fi, computer monitors, and safes for secure storage, ensuring that guests have all the tools necessary for their remote work needs. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Greenwich holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Greenwich with parking available—perfect for families or travellers 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 rental amenities include essential kitchen appliances such as microwaves and dishwashers, along with cookware, dishware, and utensils to facilitate home cooking. Additionally, most rentals also feature refrigerators to store food and beverages.
When is the best time to visit Greenwich for a holiday rental?
The best time to visit Greenwich for a holiday rental is during the peak season from May to July. This vibrant period attracts travellers, drawn by the picturesque coastal scenery and a plethora of outdoor activities. With warm temperatures averaging in the high 20s Celsius, it's great for enjoying the beautiful parks, waterfront views, and local events that make Greenwich so appealing.

July stands out as the most popular month, offering an exciting atmosphere filled with summer festivities, including outdoor concerts and community events. Visitors can take advantage of the lush landscapes for leisurely strolls or picnics in the many parks, such as the scenic Greenwich Point Park, where you can relax by the beach or explore the trails.

For those mindful of their budget, consider visiting in December. While this marks the low season, it presents a unique opportunity to experience Greenwich's charming holiday decorations and festive spirit without the crowds. The town is beautifully lit with holiday displays, and you can enjoy a quieter pace while exploring the local shops and cafés.
How early should I book a Greenwich holiday rental?
Book your Greenwich holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Greenwich?
Greenwich, Connecticut, offers various attractions that highlight its rich history and picturesque landscapes. The Greenwich Avenue area is a vibrant hub featuring upscale shops, cafes, and art galleries, making it great for leisurely strolls. Nearby, the Bruce Museum showcases art and natural history, providing an engaging experience for visitors of all ages.

For those interested in outdoor activities, the scenic Greenwich Point Park, also known as Tod's Point, is a beautiful location for walking, picnicking, and enjoying views of Long Island Sound. The area features sandy beaches and trails great for exploring. Furthermore, the historic Bush-Holley House, located in the Cos Cob neighbourhood, offers a glimpse into the town's artistic past with its impressive collection of American art and beautiful gardens.
Can I change or cancel my Greenwich home rental booking on Vrbo?
To find Greenwich holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, 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 organising 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.

More holiday ideas