Discover Your Perfect Greenwich Vacation Homes

Greenwich Luxury Rentals

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Greenwich Pet Friendly Vacation Rentals

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Greenwich Large Vacation Homes

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Why Choose Rent By Owner for your Greenwich Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Greenwich Vacation Rentals

Where are the best neighborhoods to stay in Greenwich?

When choosing where to stay in Greenwich, Connecticut, you'll find neighborhoods that perfectly blend charm and convenience. From the tranquil residential streets to lively districts with easy access to local amenities, each area offers a unique experience tailored to your preferences. Whether you prefer a peaceful retreat or a lively community atmosphere, exploring the neighborhoods in Greenwich will help you discover the ideal setting for your getaway. Enjoy the seamless booking process and reliable options that make your stay in Greenwich both memorable and hassle-free.

North Stamford

In this part of the region, you can enjoy a tranquil setting while exploring the nearby natural landscapes and local amenities. It's an ideal spot to find comfortable vacation rentals that offer both convenience and a peaceful retreat.

View 187+ Rentals in North Stamford

Best Times to Visit Greenwich

When should you plan your Vacation Rentals stay?

Choosing the ideal time to vacation in Greenwich ensures you experience the area's natural beauty and local charm at its best, whether you're seeking vibrant seasonal events or tranquil retreats during quieter months.

Peak Season Highlights

summer
Summer (June to August)

During the peak summer months, you can enjoy longer daylight hours and warm weather, making it ideal for exploring the scenic outdoors and local culture of this destination.

Average Temperature Daytime: around 80°F - Nighttime: around 65°F
autumn
Fall (September to November)

The fall season offers vibrant foliage and mild temperatures, attracting visitors who want to experience the natural beauty of the region during its most colorful time of year.

Average Temperature Daytime: around 70°F - Nighttime: around 50°F

Off-Season Highlights

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Winter (December to February)

With colder temperatures and fewer crowds, winter is a peaceful time to enjoy cozy stays and explore indoor attractions in this area.

Average Temperature Daytime: around 40°F - Nighttime: around 25°F
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Early Spring (March to April)

Before the full bloom of spring, early spring offers quieter surroundings and still mild weather, perfect for those seeking a more relaxed visit.

Average Temperature Daytime: around 50°F - Nighttime: around 35°F

Weekly Weather Forecast for Greenwich

How to Book Your Greenwich Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Greenwich

More Top-Rated Vacation Rentals in Greenwich Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining with a private patio or grill area to make the most of your visit.
  • Take advantage of beautifully landscaped gardens or lawns for relaxing or outdoor activities.
  • Make use of a spacious backyard ideal for family gatherings or outdoor play.
  • Benefit from access to communal swimming pools or hot tubs during certain seasons.
  • Relax on a charming porch or veranda that offers peaceful views of the surrounding scenery.
  • Explore scenic walking trails or paths directly accessible from the property.
  • Experience the comfort of a fire pit area perfect for evenings outdoors with friends or family.

Top Attractions Around Greenwich

What attractions are nearby?

In this charming destination, you can enjoy a variety of outdoor activities and cultural experiences just moments from your vacation rentals, allowing you to immerse yourself in the best that the area has to offer.

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Family Activities

  • Greenwich Point Park: Enjoy a family picnic and a day at the beach in this scenic park, offering stunning views of the Long Island Sound and easy access for children to play along the shoreline.
  • The Maritime Center at Greenwich: Explore maritime history through engaging exhibits and hands-on activities that entertain and educate children about the area’s nautical heritage.
  • Bruce Museum of Arts and Science: Discover art and natural science under one roof with interactive exhibits and family-friendly programs designed to inspire curiosity in young visitors.
  • : Relax and play in this lush green space featuring walking trails, playgrounds, and open areas perfect for family outings and outdoor fun.
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Adult Activities

  • Visit the Greenwich Point Park: Relax and enjoy outdoor activities like walking along the shoreline or picnicking in this scenic coastal park that offers stunning views of Long Island Sound.
  • Explore the Bruce Museum: Discover a blend of natural history, science, and art exhibits that provide an enriching experience right in the heart of the area.
  • Experience the Greenwich Avenue Shopping: Indulge in upscale boutiques, charming cafes, and unique shops in this vibrant shopping district known for its fashionable atmosphere.
  • Attend a performance at the Greenwich Symphony: Enjoy live classical music concerts that showcase talented local and regional performers within this culturally rich destination.

Other Places to Stay in Greenwich, CT

Griffith E. Harris Golf Course
Griffith E. Harris Golf Course Vacation Rentals
Audubon Center
Audubon Center Vacation Rentals
Stanwich Club
Stanwich Club Vacation Rentals
Putnam Cottage
Putnam Cottage Vacation Rentals
Bruce Museum of Arts and Science
Bruce Museum of Arts and Science Vacation Rentals
Greenwich Ferry Dock
Greenwich Ferry Dock Vacation Rentals
Cavalier Galleries
Cavalier Galleries Vacation Rentals
Greenwich Avenue Historic District
Greenwich Avenue Historic District Vacation Rentals
Greenwich Avenue
Greenwich Avenue Vacation Rentals
Flinn Gallery at Greenwich Library
Flinn Gallery at Greenwich Library Vacation Rentals
Greenwich Municipal Center Historic District
Greenwich Municipal Center Historic District Vacation Rentals
Greenwich Hospital Association
Greenwich Hospital Association Vacation Rentals
More Places to Stay Near Greenwich

Greenwich Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Take advantage of nearby cultural and natural sites to maximize your experience in this scenic region.
  • Plan Your Transportation: Arrange reliable transportation options in advance to easily access key areas and avoid unnecessary delays.
  • Enjoy Culinary Delights: Discover the area's diverse dining scene to indulge in local flavors and enhance your stay.
  • Book Thoughtfully: Secure your preferred vacation rentals early for a seamless experience, ensuring comfort and convenience during your visit.

Transportation Options

  • Greenwich Metro-North Railroad Station: This commuter rail service offers convenient access to New York City and other regional destinations, making it easy to explore beyond this scenic area.
  • Local Bus Services: Numerous bus routes operate within the region, providing affordable and reliable transportation options for getting around here efficiently.
  • Taxi and Rideshare Services: Taxis and popular rideshare apps are readily available in this destination, offering flexible transportation directly from your vacation rental.
  • Car Rentals: Having a rental car allows you the freedom to explore the region at your own pace, with several local providers conveniently located nearby.

Local Customs Options

  • Greenwich Village Fair: During the local fair, you'll find traditional crafts and foods that reflect the area's rich cultural heritage.
  • Seafood Dining Etiquette: When dining at waterfront establishments, it's customary to enjoy fresh seafood with a respectful nod to maritime traditions.
  • Seasonal Decorations: The region celebrates changing seasons with festive decorations that honor its historical seasonal customs.
  • Community Celebrations: Participating in neighborhood parades and gatherings offers insight into the community-centered spirit of Greenwich here.

Frequently Asked Questions About Greenwich?

1. What are the top vacation rentals in Greenwich?

There are a lot of options in Greenwich. If you plan on staying in the Greenwich area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Greenwich:

2. Which vacation homes in Greenwich are best for families?

If you are looking for a family-friendly vacation home in Greenwich, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Greenwich:

3. How many Rentbyowner vacation rentals are available in Greenwich?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 71 in the Greenwich area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Greenwich. 

4. What is the cancellation policy for vacation rentals in Greenwich, Connecticut?

Cancellation policies vary by property, so it's essential to review the specific listing details or contact the owner directly to understand the applicable terms and any potential fees.

5. Are there any special requirements or deposits needed when booking a vacation rental in the area?

Some properties may require security deposits or additional fees. To ensure a smooth booking process, check the listing for specific requirements or reach out to the owner for clarification.

6. How do I find the most suitable vacation rental in Greenwich that meets my needs?

Utilize the search filters and read guest reviews on the listing page to identify a property that aligns with your preferences, including location, amenities, and budget.

7. What should I know about checking in and checking out of vacation rentals here?

Check-in and check-out procedures vary by property; details are typically provided in the listing. Contact the owner if you need specific instructions or have scheduling concerns.

8. Is it possible to modify or extend my stay at a vacation rental in this destination?

Modifications or extensions depend on the owner's policies and current availability. Reach out directly to the host to discuss your plans and obtain confirmation.