Old Saybrook holiday lettings

We found 422 holiday rentals — enter your dates for availability

Select from 54 homes, 21 cottages and other holiday rentals in Old Saybrook to find one that's perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include parking and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Old Saybrook

Showing deals for:20 Feb - 27 Feb

Image gallery for Family Cottage Steps from the Beach!

Exterior
9.8 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)

Family Cottage Steps from the Beach!

Niantic, CT

7% off
Price is £2,681
for 7 nights, 1 cottage
£383 per night
includes taxes & fees
Family Cottage Steps from the Beach!

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Travel to scenic Old Saybrook

Enjoy the history and other features of Old Saybrook. This city is scenic and relaxing, recognised for its beaches, golfing and shopping. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Old Saybrook

Do you want to find top things to see and do in the city? Venture out of your cosy holiday rental and experience everything that Old Saybrook has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Dinosaur Place at Nature's Art (12.3 mi / 19.9 km)
  • Kontokosta Winery (12.6 mi / 20.2 km)
  • Machimoodus State Park (14.7 mi / 23.7 km)
  • Stay and Play LLC (0.5 mi / 0.8 km)
  • Chamard Vineyards (8.7 mi / 14 km)
  • The Book Barn (8.9 mi / 14.4 km)

Exploring the beaches and other natural features in Old Saybrook

Whether you're an outdoor enthusiast or just want to take in the scenery, Old Saybrook is a great place to get outside. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Harvey's Beach (1.9 mi / 3 km)
  • Goose Island (3.1 mi / 4.9 km)
  • Westbrook Town Beach (4.3 mi / 7 km)
  • McCook Point Beach (9.3 mi / 15 km)
  • Hammonasset Beach (9.4 mi / 15.1 km)
  • Hole-in-the-Wall Beach (9.6 mi / 15.4 km)

Seasonal weather averages in Old Saybrook

If you're planning a holiday around warm-weather activities, July, August, June and September are the hottest months to visit, when temperatures average 21°C.

How to get to and around Old Saybrook

The nearest airport is in New London, CT (GON-Groton - New London), located 17.3 mi (27.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Fishers Island, NY (FID-Elizabeth Field), which is 18.3 mi (29.4 km) away.

If you prefer train travel, the main station serving the city is Old Saybrook Station.

Frequently asked questions

What is the best area to stay in Old Saybrook when booking a holiday rental?
When considering a holiday rental in Old Saybrook, Connecticut, the best area to stay in is the charming neighbourhood of Saybrook Point. This picturesque waterfront area offers a delightful blend of scenic views and convenient access to local attractions. Nestled at the confluence of the Connecticut River and Long Island Sound, Saybrook Point is not only beautiful but also bustling with activities. You can enjoy leisurely strolls along the waterfront and take in the stunning views from the Saybrook Breakwater Lighthouse.

Another appealing option is the Old Saybrook Village, which is known for its quaint shops, inviting cafés, and rich history. Here, you'll find the Old Saybrook Historical Society and the Katharine Hepburn Cultural Arts Centre, both of which celebrate the town's vibrant heritage. This area typically boasts a variety of holiday rentals, ranging from cosy cottages to charming apartments, making it easy to find a suitable accommodation.
How much does it cost to rent a holiday home in Old Saybrook?
Prices for holiday rentals in Old Saybrook 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 Old Saybrook 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 Old Saybrook holiday house rentals?
You can find great discounts on house rentals in Old Saybrook 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 Old Saybrook?
For renting a beach house in Old Saybrook, Connecticut, the area around the Old Saybrook Point is particularly appealing, as it provides stunning views of the Connecticut River and Long Island Sound. This coastal neighbourhood offers a variety of holiday rentals, many of which feature amenities such as spacious decks, private docks, and outdoor dining areas, making them superb for enjoying the seaside atmosphere. Some properties also come equipped with modern kitchens and ample living space, ideal for families or groups seeking a beach getaway.

Another excellent area to consider is the neighbourhood near Harvey's Beach, which is known for its sandy shores and calm waters, suitable for swimming and sunbathing. Here, travellers can find charming beach cottages that often include outdoor showers, BBQ grills, and quick access to the beach, enhancing the overall holiday experience. This area is also close to local shops and eateries, providing convenient dining options.
What is the most popular type of holiday rental accomodation in Old Saybrook?
In Old Saybrook, holiday houses are the most popular type of rental, with around 47 available throughout the area. These properties are often situated in serene neighbourhoods, providing a peaceful escape while being close to local attractions such as the historic Old Saybrook Lighthouse and the scenic Saybrook Point. Most holiday houses come equipped with multiple bedrooms, fully stocked kitchens, and spacious living areas, great for families or groups looking to relax together.
Are there any family house rentals in Old Saybrook?
In Old Saybrook, Connecticut, there are numerous family-friendly house rentals available—around 49 in total. This charming coastal town offers a delightful mix of beach access and historic attractions, making it an excellent choice for families. Many of the properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to enjoy.

Visitors can find homes with amenities such as private gardens, decks for barbecues, and some even come with game rooms, ensuring entertainment for all ages. Families will appreciate the proximity to local highlights like the scenic Saybrook Point and the picturesque beaches along the Long Island Sound, great for a day of sun and sand.
Can I find long-stay holiday rentals in Old Saybrook?
A long-stay holiday rental in Old Saybrook 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 Old Saybrook?
In Old Saybrook, there are a variety of pet-friendly house rentals available, with approximately 21 options to choose from. Many of these holiday homes feature spacious interiors and outdoor areas, allowing pets to roam freely. Travellers can expect amenities such as fully equipped kitchens, comfortable living spaces, and sometimes private gardens or patios that are great for enjoying the fresh air with their furry companions.

The neighbourhood is ideally located near several pet-friendly points of interest, including the scenic Saybrook Point Park, which provides lovely walking paths along the waterfront, great for leisurely strolls with pets. Additionally, the nearby Harvey's Beach is a delightful spot for a day out, where pets can enjoy the sandy shore alongside their owners.
Are there any remote work holiday rentals in Old Saybrook?
In Old Saybrook, Connecticut, there are numerous options for remote work holiday rentals, with around 58 available to choose from. This picturesque coastal town offers a charming backdrop for working away from home, with many properties equipped with amenities tailored for productivity. Expect accommodations that feature dedicated office spaces, desks, and comfortable chairs, ensuring a conducive work environment. Additionally, many rentals include high-speed Wi-Fi and laptop workspaces, allowing for seamless connectivity during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Old Saybrook holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Old Saybrook 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 Old Saybrook?
In Old Saybrook, popular holiday rentals typically feature essential amenities that enhance the comfort of your stay. Most properties include a well-equipped kitchen, allowing guests to prepare their own meals, along with a refrigerator and microwave for convenience. Cookware, dishware, and utensils are also commonly provided, ensuring that visitors have everything they need to dine in.
When is the best time to visit Old Saybrook for a holiday rental?
The best time to visit Old Saybrook for a holiday rental is during the summer months of June to August, with July being particularly popular among travellers. This vibrant period is characterised by warm temperatures averaging around 27°C, making it ideal for enjoying outdoor activities by the picturesque Connecticut shoreline. Visitors can indulge in a variety of activities, from sunbathing on the sandy beaches to exploring the charming local shops and dining at waterfront restaurants.

The peak season attracts families and beach enthusiasts, creating a lively atmosphere filled with events and community activities. You'll find the beautiful Saybrook Point, where you can enjoy stunning sunsets and take leisurely strolls along the scenic waterfront.

For those looking for a more budget-friendly experience, consider visiting in November. This month offers a quieter charm as the summer crowds disperse, allowing for peaceful walks along the beach and the opportunity to enjoy the crisp autumn air while witnessing the changing leaves.
How early should I book a Old Saybrook holiday rental?
Book your Old Saybrook 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 Old Saybrook?
In Old Saybrook, visitors can explore a range of attractions that highlight the town's coastal charm and rich history. The Old Saybrook Historical Society offers insights into the town's past, while the nearby Katherine Hepburn Cultural Arts Centre hosts performances and events. The picturesque Saybrook Point is ideal for leisurely strolls and features stunning views of the Connecticut River as it meets the Long Island Sound. Holiday rentals in this area often provide convenient access to local beaches, such as Main Beach and Harvey's Beach, where guests can enjoy sunbathing and swimming.
Can I change or cancel my Old Saybrook home rental booking on Vrbo?
To find Old Saybrook 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 Old Saybrook 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.

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