Best Vacation Homes in Old Greenwich
7 Guests
3 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $588/Night
For 7 Nights US $4,114
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Fireplace/Heating
- View
- Kitchen
US $95/Night
For 7 Nights US $662
1 Bedroom
1 Bathroom
Family Friendly
Bed & Breakfast
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $235/Night
For 7 Nights US $1,646
6 Guests
3 Bedrooms
2 Bathrooms
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
US $424/Night
For 7 Nights US $2,970
1151.74 ft²
5 Guests
2 Bedrooms
2 Bathrooms
Pet Friendly
Apartment
- Private Pool
- Fireplace/Heating
- Pool
US $249/Night
For 7 Nights US $1,743
1000 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $143/Night
For 7 Nights US $998
4 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
US $211/Night
For 7 Nights US $1,476
550 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $316/Night
For 7 Nights US $2,214
Old Greenwich Luxury Rentals
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $2,642/Night
For 7 Nights US $18,494
2895.49 ft²
20 Guests
5 Bedrooms
3 Bathrooms
House
- Fireplace/Heating
- Balcony/Terrace
- View
US $1,914/Night
For 7 Nights US $13,396
10 Guests
6 Bedrooms
6 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,908/Night
For 7 Nights US $13,353
10 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $1,898/Night
For 7 Nights US $13,283
2497.23 ft²
14 Guests
7 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- View
- Parking
US $1,282/Night
For 7 Nights US $8,974
3050 ft²
5 Guests
3 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,192/Night
For 7 Nights US $8,343
3000 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $1,169/Night
For 7 Nights US $8,182
516.67 ft²
4 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Pet Friendly
- Parking
US $1,108/Night
For 7 Nights US $7,756
Old Greenwich Pet Friendly Vacation Rentals
3 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $335/Night
For 7 Nights US $2,345
796.53 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $320/Night
For 7 Nights US $2,237
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Air Conditioner
US $147/Night
For 7 Nights US $1,029
3 Guests
2 Bedrooms
1 Bathroom
Ocean View
Apartment
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $282/Night
For 7 Nights US $1,976
1044.1 ft²
5 Guests
1 Bedroom
2 Bathrooms
Family Friendly
Apartment
- Private Pool
- Fireplace/Heating
- Pool
US $287/Night
For 7 Nights US $2,009
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $274/Night
For 7 Nights US $1,915
775 ft²
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Private Pool
- Fireplace/Heating
- Pool
US $347/Night
For 7 Nights US $2,429
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $178/Night
For 7 Nights US $1,248
Old Greenwich Large Vacation Homes
2800 ft²
20 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $998/Night
For 7 Nights US $6,985
1743.75 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Villa
- Fireplace/Heating
- Balcony/Terrace
- View
US $393/Night
For 7 Nights US $2,751
10 Guests
5 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $971/Night
For 7 Nights US $6,800
850.35 ft²
5 Guests
1 Bedroom
1 Bathroom
Villa
- Fireplace/Heating
- Balcony/Terrace
- View
US $177/Night
For 7 Nights US $1,238
2800 ft²
12 Guests
4 Bedrooms
2 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $773/Night
For 7 Nights US $5,410
11 Guests
3 Bedrooms
1 Bathroom
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
US $756/Night
For 7 Nights US $5,292
2500 ft²
14 Guests
7 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,030/Night
For 7 Nights US $7,210
8 Guests
5 Bedrooms
5 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Pool
US $600/Night
For 7 Nights US $4,200
Why Choose Rent By Owner for your Old Greenwich Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Old Greenwich
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit ensures you experience the best of this charming destination, allowing you to enjoy its seasonal beauty and local ambiance while making the most of your vacation rental here in the region.
Peak Season Highlights
Summer (June to August)
During the peak summer months, this destination experiences warm weather, making it ideal for enjoying outdoor activities and exploring the scenic coastline.
Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 70°F
Fall (September to November)
Autumn is a popular time when the region's vibrant foliage attracts visitors seeking picturesque views and pleasant weather.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F
Off-Season Highlights
Winter (December to February)
The winter months bring cooler temperatures with fewer crowds, offering a peaceful retreat for those looking to enjoy the area's quiet charm.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 25°F to 35°F
Spring (March to May)
In early spring, the area begins to warm up, yet the shoulder season delivers a tranquil experience before the summer rush begins.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 40°F to 50°F
Weekly Weather Forecast for Old Greenwich
How to Book Your Old 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 Old Greenwich
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 a spacious outdoor patio or deck perfect for relaxing or entertaining guests amidst scenic surroundings.
- Take advantage of a private garden or yard to unwind and appreciate the fresh air during your stay.
- Benefit from access to a charcoal or gas grill, ideal for hosting outdoor cookouts with friends or family.
- Discover a dedicated outdoor dining area that makes alfresco meals a memorable experience in this region.
- Experience a well-maintained swimming pool or hot tub for ultimate relaxation after exploring nearby attractions.
- Make use of outdoor recreational facilities such as tennis courts or a basketball hoop, suitable for active pursuits.
- Relax on outdoor furniture set within a landscaped space, allowing you to soak up the area's natural beauty.
Top Attractions Around Old Greenwich
What attractions are nearby?
Within this charming area, you can enjoy a variety of outdoor activities, cultural experiences, and seaside strolls that highlight the best of what nearby Old Greenwich offers for an enriching and memorable stay.
Family Activities
- Greenwich Point Park: Enjoy a day of family fun at this scenic park, where you can relax on the sandy beaches and explore nature trails along the water.
- Bush-Holley House Museum: Step back in time with your family at this historic museum that offers engaging tours and educational programs highlighting local history.
- Binney Park: Picnic, play, or take a leisurely walk in this beautiful neighborhood park designed for family gatherings and outdoor activities.
- Old Greenwich Community Center: Participate in family-friendly classes and events at this hub of community activity, perfect for making memories together here in the region.
Adult Activities
- Explore Greenwich Point Park: Enjoy a relaxing day at this scenic waterfront park, perfect for walking along the trails or unwinding on the sandy beaches.
- Visit the Bruce Museum: Immerse yourself in local art and natural history exhibits that showcase the region's rich cultural heritage.
- Attend a performance at the Palace Theater: Experience live entertainment in an intimate setting, celebrating the arts within the heart of this charming destination.
- Discover local boutiques and eateries: Stroll through the quaint shopping districts to find unique shops and dine at highly-rated restaurants that highlight regional flavors.
Other Places to Stay in Old Greenwich, CT
Greenwich Point Park
Old Greenwich Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the area's renowned eateries to enjoy authentic regional flavors during your stay.
- Visit Nearby Beaches: Relax and unwind by spending time at the local beaches, which offer a perfect escape for leisure and scenic views.
- Discover Community Events: Stay informed about seasonal festivals and events that provide a genuine taste of this destination's vibrant culture.
- Plan Outdoor Activities: Make the most of the region’s parks and nature trails for outdoor adventures that suit all interests and fitness levels.
Transportation Options
- Metro-North Railroad: This commuter train service offers convenient access to New York City and nearby areas, making it an ideal transportation option for exploring the region from your vacation rental.
- Local Bus Services: Regional buses connect Old Greenwich to surrounding communities and offer a cost-effective way to navigate the area without the need for a car.
- Taxis and Rideshare Services: Taxis and popular ride-sharing companies provide flexible, door-to-door transportation options for quick trips within the region or to nearby destinations.
- Car Rentals: Renting a vehicle offers the freedom to explore all that this destination has to offer at your own pace, with numerous local agencies available nearby.
Local Customs Options
- Greenwich Time-Honored Traditions: Participating in local celebrations often involves embracing timeless Greenwich customs, giving you an authentic experience of the area's cultural heritage.
- Seasonal Festivals and Parades: During various times of the year, community parades and festivals highlight regional pride and bring residents and visitors together in the region's welcoming atmosphere.
- Seaside Dining Etiquette: When enjoying waterfront dining here, you’ll notice a relaxed yet refined approach to service that reflects the region’s maritime roots.
- Historic Preservation Practices: Respect for historic architecture and landmarks is evident in the way locals preserve their homes and public spaces, providing a glimpse into the area's rich history.
Old Greenwich Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Old Greenwich?
There are a lot of options in Old Greenwich. If you plan on staying in the Old 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 Old Greenwich:
- Lower Lvl Private 2BR/1BA Family/Pet Friendly
- Lovely 2 bdrm apt w/parking and outdoor sitting
- New Beach Home near Stamford Downtown/Shippan
- Boutique Stay 2C in Heart of Downtown
- Penthouse Perfection: with Unmatched Skyline Views
- Seabreeze at the beach west beach Stamford ct.
- Greenwich, CT Hotel Alternative Completely Renovated High End Townhouse
- Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
- Spacious 5BR Old Greenwich Village Home - Walk/Bike to Beach, Train to NYC
- Best hotel alternative for big group, near train
2. How many vacation rentals have private pools in Old Greenwich?
There are 5 vacation rentals with private pools near Old Greenwich. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Old Greenwich are best for families?
If you are looking for a family-friendly vacation home in Old 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 Old Greenwich:
4. How many Rentbyowner vacation rentals are available in Old Greenwich?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 294 in the Old 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 Old Greenwich.
5. What is the cancellation policy for booking a vacation rental in Old Greenwich?
Cancellation policies vary by property owner, so it’s important to review the specific listing details before booking. You can find this information on the listing page or contact the owner directly for clarification.
6. How do I confirm the availability of a vacation rental in Old Greenwich?
Availability updates in real-time on the listing pages. Once you select your dates, you can see if the property is available or reach out to the owner for confirmation before completing your reservation.
7. What amenities are typically included in vacation rentals here?
The amenities depend on the specific property, but common features often include Wi-Fi, parking, kitchen facilities, and outdoor space. Detailed amenities are listed on each property’s page, and you can contact the owner for any special requests.
8. Are there any house rules I should be aware of when booking in this destination?
House rules are specified by the property owner and can be found on the listing page. It’s advisable to read these rules carefully before booking to ensure your stay complies with their requirements.
9. How do I contact the property owner if I have questions about my stay in Old Greenwich?
You can message the owner directly through the platform’s messaging system. They will be able to provide detailed information about the property, local area, and any specific concerns you might have.
Old Greenwich Top Rated Vacation Rentals
754 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Private Pool
- Fireplace/Heating
- Pool
US $333/Night
For 7 Nights US $2,333
731.94 ft²
9 Guests
20 Bedrooms
2 Bathrooms
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Pool
US $526/Night
For 7 Nights US $3,679
1 Bedroom
1 Bathroom
Ocean View
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
US $298/Night
For 7 Nights US $2,085
342.79 ft²
40 Guests
19 Bedrooms
19 Bathrooms
Group Friendly
Hotel
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $421/Night
For 7 Nights US $2,944
US $310/Night
For 7 Nights US $2,168
1 Bedroom
1 Bathroom
Ocean View
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
US $237/Night
For 7 Nights US $1,658
473.61 ft²
16 Guests
159 Bedrooms
2 Bathrooms
Family Friendly
Hotel
- Private Pool
- Spa
- Pool
US $302/Night
For 7 Nights US $2,114
344.45 ft²
16 Guests
20 Bedrooms
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
US $265/Night
For 7 Nights US $1,855
