1. USA
  2. Connecticut
  3. Old Saybrook
  4. Rentals by Owner

Discover Your Perfect Old Saybrook Rentals by Owner

Old Saybrook Rentals by Owner

More Top-Rated Rentals by Owner in Old Saybrook Area

Why Choose Rent By Owner for your Old Saybrook vacation rental?

What makes our Rentals by Owner special?

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

Popular Areas for Old Saybrook Rentals by Owner

Where are the best neighborhoods to stay in Old Saybrook?

Exploring the neighborhoods in Old Saybrook, Connecticut, allows you to find the perfect rental by owner that suits your vacation style. Whether you prefer staying near tranquil waterfront areas or charming historic districts, each neighborhood offers a unique experience rooted in the town’s rich maritime heritage and scenic beauty. When booking your stay through Rent By Owner, you can select from a variety of trusted accommodations nestled within these inviting communities, ensuring a seamless and dependable vacation experience in this picturesque New England town.

Saybrook Manor

In this neighborhood, you'll find a tranquil setting perfect for relaxing getaways, with easy access to the scenic coast and local amenities. It's an ideal choice if you're seeking a peaceful retreat within the region's charming surroundings.

View 26+ Rentals in Saybrook Manor

Westbrook Center

Located near the heart of Westbrook, this area offers convenient proximity to shopping, dining, and cultural attractions, making it a practical base for exploring the region's vibrant community and natural beauty.

View 89+ Rentals in Westbrook Center

Madison Center

This lively neighborhood is known for its welcoming atmosphere and close-knit community, providing a perfect setting for those wanting to enjoy both local charm and easy access to nearby beaches and parks.

View 84+ Rentals in Madison Center

Old Saybrook Center

Situated at the core of the town, this neighborhood offers travelers a central location with convenient access to shops, restaurants, and the town’s historic sites, ideal for immersing yourself in the area's coastal character.

View 51+ Rentals in Old Saybrook Center

Deep River Center

Surrounded by picturesque landscapes, this neighborhood provides a quiet environment complemented by charming boutiques and local eateries, perfect for experiencing the region's laid-back vibe.

View 25+ Rentals in Deep River Center

Chester Center

Nestled along the riverfront, Chester Center combines small-town hospitality with scenic views, making it a memorable spot for enjoying the region’s historic charm and waterfront serenity.

View 49+ Rentals in Chester Center

Best Times to Visit Old Saybrook

When should you plan your Rentals by Owner stay?

Finding the ideal time to vacation here ensures you enjoy this destination's best weather and local events, helping you select the perfect rental by owner through Rent By Owner for a memorable stay in Old Saybrook, Connecticut, USA.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

During these months, the area experiences warm temperatures ideal for enjoying outdoor activities and the scenic coastal environment.

Average Temperature Daytime: 70-80°F - Nighttime: 55-65°F
summer
Late Summer to Early Fall (August to September)

This period offers pleasant weather with less humidity, making it a popular time for visitors seeking comfortable beachside stays and local events.

Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F

Off-Season Highlights

image
Winter (December to February)

The colder months see fewer travelers in this region, providing a quiet retreat with cozy rental options and scenic winter views.

Average Temperature Daytime: 35-45°F - Nighttime: 20-30°F
image
Early Spring (March to April)

As the region transitions out of winter, prices tend to be more affordable and rental owners are more available, offering a good opportunity for budget-conscious travelers.

Average Temperature Daytime: 45-55°F - Nighttime: 30-40°F

Weekly Weather Forecast for Old Saybrook

How to Book Your Old Saybrook vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Saybrook

More Top-Rated Rentals by Owner in Old Saybrook Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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

  • Access to a spacious outdoor patio or deck for entertaining and relaxing in the fresh air.
  • Private gardens or landscaped yards that allow you to enjoy the natural beauty of the area.
  • Outdoor dining areas, perfect for enjoying meals with views of the region's scenic surroundings.
  • Grilling stations or barbecue grills to enhance your outdoor dining experience.
  • Ample outdoor seating options such as loungers or benches to unwind amid the natural environment.
  • Spaces designed for outdoor recreation, including areas for lawn games or activities.
  • Proximity to waterfront access or outdoor water features, ideal for enjoying the region’s serene waterways.

Top Attractions Around Old Saybrook

What attractions are nearby?

In this charming area, you can enjoy a variety of outdoor activities and cultural experiences that highlight the best of what the region has to offer, making it an ideal destination for your next getaway.

image
image

Family Activities

  • Saybrook Point Lighthouse & Maritime Center: Discover the region's maritime history and enjoy scenic views perfect for family photos at this historic lighthouse.
  • Keeseville Park & Beach: Relax and play on the sandy shores, where you can swim, have a picnic, or take a leisurely stroll along the shoreline.
  • Old Saybrook Historical Society & Museum: Engage with local history through interactive exhibits that are educational and entertaining for families seeking cultural experiences.
  • Essex Steam Train & Riverboat Excursions: Embark on a scenic train ride and river cruise that offer an exciting way to explore the area's natural beauty as a family adventure.
image

Adult Activities

  • Exploring the Connecticut River Museum: Discover local history and enjoy scenic views along the river, perfect for a relaxing day in this charming region.
  • Shopping at local boutiques and galleries: Browse unique shops and art galleries that showcase the area's vibrant arts scene and distinctive craftsmanship.
  • Dining in waterfront restaurants: Savor fresh seafood and regional cuisine while enjoying picturesque waterside dining experiences in the town.
  • Enjoying outdoor recreation at Saybrook Point Park: Take a leisurely walk or kayak along the shoreline, immersing yourself in the natural beauty of the area.

Other Places to Stay in Old Saybrook, CT

Middlesex County
Explore 383 Properties
Westbrook Center
Explore 89 Properties
Westbrook
Explore 89 Properties
Madison Center
Explore 84 Properties
Clinton
Explore 60 Properties
Old Saybrook Center
Explore 51 Properties
Madison
Explore 49 Properties
East Haddam
Explore 47 Properties
Haddam
Explore 38 Properties
Killingworth
Explore 29 Properties
Saybrook Manor
Explore 26 Properties
Deep River Center
Explore 25 Properties
More Places to Stay Near Old Saybrook

Old Saybrook Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local waterfronts: Take advantage of the region’s scenic shoreline by visiting nearby beaches and marinas to enjoy the tranquility and natural beauty of the area.
  • Engage with community events: Check out seasonal festivals or local markets to immerse yourself in the area's vibrant culture and support small businesses.
  • Plan outdoor activities: Make the most of the area's abundant parks and nature reserves for activities like hiking and birdwatching that showcase the region's natural charm.
  • Book accommodations early: Secure your rental by owner well in advance to access the best properties and ensure a seamless stay here in the region.

Transportation Options

  • Old Saybrook Train Station: This station offers convenient rail service connecting you to major cities along the Northeast Corridor, making travel into and out of the area straightforward.
  • Local Bus Services: The region is served by bus routes that provide reliable transportation around Old Saybrook and nearby towns, ideal for exploring without a car.
  • Rental Car Options: Several rental agencies operate here, giving you flexible options to explore the surrounding Connecticut coastline at your own pace.
  • Taxi and Ride-Sharing Services: Taxis and ride-sharing platforms are readily available in the area, offering door-to-door service for quick and easy transportation during your stay.

Local Customs Options

  • Welcome & Greetings: Visitors often exchange warm welcomes and greetings as a sign of hospitality typical in this welcoming community.
  • Community Events: Participating in local festivals and seasonal gatherings reflects the area's vibrant community spirit and rich traditions.
  • Respect for Nature: Respect for the natural surroundings is commonly observed, especially during outdoor activities along the picturesque shoreline.
  • Dining Etiquette: Enjoying locally sourced seafood and following regional dining customs can enhance your experience here.

Frequently Asked Questions About Old Saybrook Rentals by Owner

1. What are the top vacation rentals in Old Saybrook?

There are a lot of options in Old Saybrook. If you plan on staying in the Old Saybrook 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 Saybrook:

2. How many Rentbyowner vacation rentals are available in Old Saybrook?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 341 in the Old Saybrook 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 Saybrook. 

3. What is the cancellation policy for a rental by owner in Old Saybrook?

Cancellation policies vary depending on the individual listing. To understand the specific terms, please review the details provided on the rental listing or contact the property owner directly before completing your reservation.

4. How do I verify the authenticity of a rental by owner in the area?

To ensure a trustworthy booking experience, check the listing details carefully, read previous guest reviews, and communicate with the owner through the platform to confirm all pertinent information before finalizing your stay.

5. Are there any additional fees when booking a rental by owner in this region?

Additional fees such as cleaning, service charges, or security deposits are typically outlined in the listing. Confirm these charges by reviewing the listing details or contacting the owner privately for clarification.

6. What amenities can I expect in a rental by owner near here?

Amenities vary by property. To find out what’s included, such as Wi-Fi, parking, or kitchen facilities, review the property listing carefully or reach out directly to the owner for specific questions.

7. How do I contact the owner if I have special requests or need assistance during my stay?

You can contact the owner directly through the messaging system provided on the booking platform. It’s recommended to discuss any special requests or concerns before confirming your reservation to ensure a smooth stay.

More Rentals You May Like Near Old Saybrook

More Top-Rated Rentals by Owner in Old Saybrook Area