Best Vacation Homes in Old Saybrook
Air Conditioner
Internet
Child Friendly
Laundry
10.0
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
10.0- Fireplace/Heating
- Balcony/Terrace
Breakfast
Parking
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly
Kitchen
10.0- Parking
- Internet
- Child Friendly
Security/Safety
10.0- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
10.0- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
10.0- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
Old Saybrook Luxury Rentals
10.0- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
10.0- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Fireplace/Heating
Pool- Balcony/Terrace
- Kitchen
Private Pool- Oceanfront
- Pool
- Ocean View
9.8- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
9.8- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
10.0- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
Old Saybrook Pet Friendly Vacation Rentals
10.0- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
10.0- View
- Pet Friendly
- Parking
- Air Conditioner
9.6- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
10.0- Oceanfront
- Fireplace/Heating
- Ocean View
- View
9.5- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
10.0- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
![Stunning Artisan Waterfall Escape [Walk to Downtown]](https://imgservice.rentbyowner.co.uk/640x287/stunning-artisan-waterf-us-chester-ha-3211062918-0.jpg)
10.0- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
10.0- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
Old Saybrook Large Vacation Homes
10.0- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
10.0- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
10.0- Private Pool
Hot Tub- Fireplace/Heating
- Pool
9.6- Oceanfront
Spa- Fireplace/Heating
- Ocean View
10.0- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
10.0- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
10.0- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Air Conditioner
10.0- Oceanfront
- Ocean View
- Balcony/Terrace
- View
Why Choose Rent By Owner for your Old Saybrook Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Old Saybrook Vacation Rentals
Where are the best neighborhoods to stay in Old Saybrook?
When planning your stay in Old Saybrook, Connecticut, choosing the right neighborhood can enhance your vacation experience. Whether you prefer a charming coastal setting or a quiet residential area, Old Saybrook offers diverse neighborhoods with unique character and easy access to local attractions. By selecting the ideal location within this historic town, you can enjoy a comfortable and memorable visit while experiencing the relaxed New England atmosphere. Discover the perfect place to stay that aligns with your vacation goals and makes your trip to Old Saybrook truly special.
Saybrook Manor
Stay in Saybrook Manor to enjoy a peaceful retreat within the region, where charming accommodations provide easy access to the area's scenic beauty and quiet neighborhoods. This neighborhood offers a relaxing atmosphere ideal for travelers seeking comfort and tranquility.
View 223+ Rentals in Saybrook ManorWestbrook Center
Westbrook Center is perfect for those looking to immerse themselves in the local community while staying close to the region's attractions. Here, you can find convenient options for your stay, blending small-town charm with accessibility to nearby beaches and parks.
View 58+ Rentals in Westbrook CenterMadison Center
By choosing Madison Center, you'll be situated in an area known for its vibrant downtown and picturesque setting, offering a great base for exploring the region’s coastal scenery. It’s an ideal spot for travelers seeking a lively yet relaxed environment.
View 91+ Rentals in Madison CenterOld Saybrook Center
Staying near Old Saybrook Center places you at the heart of the town’s historic district, providing easy access to local shops and dining options. It’s a prime location to experience the authentic charm and rich history of this region.
View 33+ Rentals in Old Saybrook CenterDeep River Center
Deep River Center offers a cozy neighborhood setting that’s perfect for discovering the region’s natural beauty and outdoor activities. Choose this area for a serene escape surrounded by lush landscapes and friendly communities.
View 63+ Rentals in Deep River CenterChester Center
Chester Center provides a quaint and inviting atmosphere, ideal for travelers wanting to explore the region’s local culture and scenic spots. Its charming surroundings make it a wonderful choice for a peaceful getaway.
View 59+ Rentals in Chester CenterBest Times to Visit Old Saybrook
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit here ensures you experience this charming destination at its best, whether it's for exploring the region’s scenic beauty or enjoying its relaxed coastal atmosphere.
Peak Season Highlights
Late Spring to Early Summer (May - June)
This is when the region experiences warm weather and longer daylight hours, making it ideal for enjoying outdoor activities and the scenic coastal views. During this period, you'll find that the area’s vacation rentals are in high demand.
Summer (July - August)
Peak summer months bring lively festivities and warm ocean breezes, perfect for beach outings and relaxing by the water. Booking early ensures you secure your preferred vacation rental during this bustling season.
Off-Season Highlights
Early Fall (September - October)
As the summer crowds fade, this time offers a quieter experience with mild temperatures and beautiful fall foliage. It’s an excellent opportunity to enjoy the area's natural beauty with more availability for vacation rentals.
Late Winter to Early Spring (February - April)
During these months, the region becomes less crowded, and the cool weather offers a peaceful retreat. It's a great time to explore the area with flexible rental options available at more affordable rates.
Weekly Weather Forecast for Old Saybrook
How to Book Your Old Saybrook Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Old Saybrook
Common Vacation Rentals Amenities
What amenities can you expect?
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 fully equipped barbecue grill area for gatherings under the open sky.
- Relax in a private backyard perfect for sunbathing, picnicking, or simply unwinding after a day exploring the region.
- Take advantage of nearby waterfront access for kayaking, paddleboarding, or scenic fishing excursions.
- Benefit from spacious patios or decks ideal for morning coffee or evening relaxation while taking in the surroundings.
- Utilize dedicated outdoor parking spaces designed for your convenience and easy access to your rental.
- Explore well-maintained gardens or landscaped lawns that enhance the outdoor experience at your stay here.
- Make the most of outdoor fire pits or fireplaces for cozy nights under the stars with friends and family.
Top Attractions Around Old Saybrook
What attractions are nearby?
While here, you can enjoy a variety of nearby activities in the region, from exploring scenic nature trails to relaxing by the waterfront, all conveniently accessible from your vacation rental in Old Saybrook, Connecticut.
Family Activities
- Old Saybrook's Maritime Museum: Discover the region’s rich nautical history through engaging exhibits that are perfect for family exploration.
- Saybrook Point Park: Enjoy outdoor family fun by strolling along scenic waterfront trails, picnicking, or participating in seasonal events in this charming area.
- The Connecticut River Museum: Immerse your family in interactive exhibits and boat tours that highlight the region’s river heritage and natural beauty.
- Old Saybrook Beaches: Relax and build sandcastles at pristine beaches where families can swim, play, and enjoy the coastal scenery together.
Adult Activities
- Old Saybrook Historic District Tour: Immerse yourself in the area's rich history by exploring well-preserved buildings and landmarks that tell the story of this charming coastal town.
- Old Saybrook Point Lighthouse Climb: Experience breathtaking views of the shoreline by visiting and climbing this iconic lighthouse, a must-do activity for those seeking scenic coastal panoramas.
- Sea Captains' Walk Walking Tour: Stroll along the picturesque waterfront and discover the stories of maritime history through guided or self-guided walks in the region.
- Local Art Galleries and Studios: Engage with the area's vibrant arts scene by visiting galleries showcasing regional artists, perfect for art lovers looking to enrich their stay here.
Other Places to Stay in Old Saybrook, CT
Old Saybrook Travel Tips
How Can You Make the Most of Your Stay?
- Explore local dining experiences: Take advantage of the region's renowned eateries to enjoy fresh, locally-sourced cuisine and immerse yourself in the area’s culinary culture.
- Visit nearby beaches: Make time for relaxing days at the nearby beaches that offer scenic views and a perfect setting for unwinding during your stay.
- Discover cultural attractions: Engage with the area's rich history and arts scene by exploring museums and galleries that showcase its unique heritage.
- Plan outdoor activities: Benefit from the region’s natural beauty by participating in outdoor pursuits like boating, hiking, or nature walks to enhance your vacation experience.
Transportation Options
- Old Saybrook Train Station: This station offers convenient Amtrak services, making it easy for you to travel along the Northeast Corridor with ease.
- Connecticut River Ferries: You can enjoy scenic ferry rides across the river, providing a relaxing and picturesque transportation option in the region.
- Local Bus Services: Local transit options connect key areas of Old Saybrook, helping you explore the town comfortably without needing a car.
- Taxi and Rideshare Services: Taxis and ride-sharing apps provide flexible, on-demand transportation, ensuring you can navigate here effortlessly during your stay.
Local Customs Options
- Welcoming Greetings: In this coastal area, it’s customary to greet neighbors and visitors with friendly waves and warm smiles, reflecting the community's welcoming spirit.
- Seafood Dining Etiquette: Locals take pride in their seafood cuisine, and sharing a meal with fresh catches is often accompanied by casual, convivial conversation.
- Preserving Local Heritage: Respect for maritime history and local traditions is evident through participation in community events and preservation efforts.
- Environmental Respect: Visitors are encouraged to practice responsible outdoor activities, ensuring the natural beauty of the region remains pristine for future generations.
Frequently Asked Questions About Old Saybrook?
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:
- Waterfront Retreat overlooking Long Island Sound w/gorgeous sunrises & sunsets!
- Saybrook Point Cottage - Charming and Private
- Wake up with Views of the Ocean
- Luxury Waterfront Home-Still some availability for Summer 2026
- The Homestead
- Birdsong - Relaxation, Activities & Culture In Quaint Shoreline Town
- Cozy cottage near downtown Clinton, Marina & Hammonasset Park
- Direct waterfront renovated cottage.
- Cozy Cottage at The Cabins
- UPDATED HOME, king+queen beds, AC, 5 min walk to beach, 1 min to Waters Edge
2. How many vacation rentals have private pools in Old Saybrook?
There are 19 vacation rentals with private pools near Old Saybrook. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Old Saybrook are best for families?
If you are looking for a family-friendly vacation home in Old Saybrook, 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 Saybrook:
4. How many Rentbyowner vacation rentals are available in Old Saybrook?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 515 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.
5. What is the cancellation policy for vacation rentals in the area?
6. How do I check the availability of vacation rentals in this destination?
7. Are there any additional fees I should be aware of when booking a vacation rental here?
8. What amenities are typically included in vacation rentals in this region?
9. Is it possible to modify or extend my stay at a vacation rental in this area?
Old Saybrook Top Rated Vacation Rentals
10.0- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
10.0- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
10.0- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
10.0- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Hot Tub
- Spa
- Fireplace/Heating
- Pool
10.0- Hot Tub
- Spa
- Fireplace/Heating
- Pool
9.8- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
