Old Saybrook holiday homes

We found 509 holiday rentals — enter your dates for availability
Select from 49 homes, 23 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:30 Oct - 6 Nov

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Why visit Old Saybrook

  • Scenic Shoreline: Enjoy the stunning Connecticut coastline with beautiful beaches and picturesque views at South Cove.
  • Historic Charm: Explore the quaint streets of Old Saybrook Centre, rich in history and local character.
  • Outdoor Activities: Take advantage of urban parks and scenic spots perfect for leisurely strolls and beach days.
  • Romantic Atmosphere: Experience the charming ambiance ideal for couples seeking a peaceful getaway.
  • Community Engagement: Connect with locals through various meetups and community events throughout the city.

Top attractions in and around Old Saybrook

Old Saybrook, Connecticut, offers a charming blend of scenic outdoor experiences and cultural attractions. Visitors can enjoy beautiful beaches, explore urban parks, and take in the picturesque views at Saybrook Point. This romantic destination is perfect for leisurely strolls, beach days, and engaging with the local community through meetups. Whether you're seeking relaxation or adventure, Old Saybrook provides a delightful backdrop for a memorable holiday.

  • Harvey's Beach: A charming local beach featuring soft sands and gentle waves, perfect for sunbathing, swimming, and picnics. Its relaxed vibe makes it an ideal spot for families and friends to unwind.
  • Harkness Memorial State Park: This expansive park offers stunning coastal views, beautiful gardens, and diverse outdoor activities such as hiking and exploring scenic trails, perfect for nature lovers.
  • Clinton Town Beach: A picturesque beach ideal for swimming and relaxing, with beautiful sunsets and a welcoming atmosphere, perfect for a leisurely day by the water.

Things to do recommended for couples

Discover the charm of Old Saybrook with your partner by taking a scenic walk along the waterfront or enjoying a sunset cruise on the Connecticut River. Explore the quaint shops and dine at a cosy restaurant, creating unforgettable memories together in this delightful coastal town.

Things to do recommended for families

In Old Saybrook, families can enjoy the scenic beauty at Harvey's Beach, explore the interactive exhibits at the Connecticut River Museum, and take a leisurely stroll along the Old Saybrook Town Green, perfect for picnics and play.

Things to do recommended for groups

Groups in Old Saybrook can experience the thrill of motor racing at Waterford Speedbowl, located 21km away. The venue offers an exhilarating atmosphere, perfect for adventure seekers looking to bond over exciting races and shared excitement.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Old Saybrook

When planning your trip—whether you're travelling with a group, family, or pets, or seeking longer stays—be sure to use the appropriate filters to align with your priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Old Saybrook with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group activities. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Old Saybrook with young kids: Travelling with young children can be quite a task. It's important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Old Saybrook: For many families, a holiday wouldn't be the same without their furry companions. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Old Saybrook: If you’re after holiday rentals with special offers for monthly or longer stays, you’ve come to the right place. Use the correct filter to easily find and save on monthly rentals, and consider including extras like a parking space, a well-equipped kitchen or a private pool in your search.

Where to stay near Old Saybrook

Old Saybrook, Connecticut, is a charming coastal city perfect for a relaxing getaway. Explore the scenic Connecticut shoreline, enjoy picturesque views at South Cove, and wander through the historic Old Saybrook Centre. With its inviting atmosphere, this destination offers a delightful blend of history and natural beauty, making it ideal for romantic holidays or family excursions. Unwind by the fireplace and soak in the tranquil vibes that this lovely city has to offer.

  • Westbrook: Located a mere 6km from Old Saybrook, Westbrook is a charming coastal city known for its stunning outdoor experiences and romantic scenery. Visitors are drawn to the beautiful beaches and family-friendly areas, perfect for a day of sun and sand. Westbrook boasts a vibrant music scene, offering concerts at various venues, and caters to golf enthusiasts with its well-maintained courses. The local attractions also include a variety of conference venues, making it an ideal spot for both leisure and business travellers looking to enjoy the scenic coastline.
  • Old Lyme: Just 5km from Old Saybrook, Old Lyme is a delightful city that invites adventurers and nature lovers alike. Its picturesque landscapes and recreational areas provide ample opportunities for outdoor activities, including hiking and mini-golf. The region is home to beautiful beaches and a national state park, making it an excellent destination for those looking to explore the great outdoors. Old Lyme's artistic community and charming atmosphere add to its appeal, offering a unique blend of adventure and culture.
  • Greenport: Situated 21km away from Old Saybrook, Greenport is a delightful coastal town renowned for its outdoor activities and romantic beach experiences. With its scenic parks and recreational areas, it’s perfect for leisurely strolls or a day in the sun. Visitors can enjoy music concerts and unwind at local golf courses. Greenport's stunning beaches and family-friendly parks are ideal for a relaxing getaway, making it a must-visit destination for those seeking a blend of relaxation and adventure.

Best time to go to Old Saybrook

If you're planning a trip to Old Saybrook, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January31.3°F (-0.4°C)Light RainMostly Sunny
February32.4°F (0.2°C)Light RainMostly Sunny
March38.5°F (3.6°C)Light RainMostly Sunny
April48.2°F (9.0°C)Light RainMostly Sunny
May57.9°F (14.4°C)Light RainMostly Sunny
June66.4°F (19.1°C)Light RainMostly Sunny
July73.8°F (23.2°C)Light RainMostly Sunny
August72.7°F (22.6°C)Light RainMostly Sunny
September66.2°F (19.0°C)Light RainMostly Sunny
October56.5°F (13.6°C)Light RainMostly Sunny
November45.5°F (7.5°C)Light RainMostly Sunny
December37.8°F (3.2°C)Light RainMostly Sunny

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can differ. Booking for a longer duration might also bring about noteworthy savings. To help you discover the ideal Vrbo property that suits your budget, simply use our filters to search by price, location, and holiday rental type.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a handy spot to start new trips, pick up where you previously left off, or organise your plans. You can easily view properties you’ve saved or booked, neatly grouped under Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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:

  • Island's End Golf and Country Club (12.1 mi / 19.4 km)
  • Chatfield Hollow State Park (12.1 mi / 19.5 km)
  • 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)
  • Sparkling Pointe (16.6 mi / 26.8 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:

  • The Hamptons Beaches (26 mi / 41.8 km)
  • Harvey's Beach (1.9 mi / 3 km)
  • Westbrook Town Beach (4.3 mi / 7 km)
  • Rocky Neck State Beach (7.1 mi / 11.4 km)
  • Clinton Town Beach (7.7 mi / 12.3 km)
  • McCook Point Beach (9.3 mi / 15 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 most popular type of holiday home accommodation in Old Saybrook?
According to our data, houses are the most desirable type of holiday home in Old Saybrook. But that goes without saying, everyone's idea of the perfect trip differs. Bookabach has holiday homes of all sizes and shapes, and we'll help you find the perfect match.
How much does it cost to rent a holiday home in Old Saybrook?
Property type, length of stay and time of year are some factors that can determine the price of a holiday home. Simply click on your dates of travel to find the ultimate escape. From homey country cottages to plush villas, all Bookabach holiday homes provide incredible value.
How much does it cost to rent a beach house in Old Saybrook?
When you travel and the style and size of the property will influence the cost of your beachside holiday home. Click on your Old Saybrook travel dates to view your available options on Bookabach. Can't live without a hot tub? Use the filters to pick the features and amenities you need.
Are there pet-friendly holiday homes in Old Saybrook?
There certainly are. You can pick from 34 holiday homes that welcome pets in Old Saybrook on Bookabach. Our furry companions deserve a getaway too, so simply use our search function for pet-friendly holiday homes to book a property where your puppy dog can join in the fun.
Can I rent a house with a pool in Old Saybrook?
Check the "pool" box in our filter tool and you'll find two houses with private pools in Old Saybrook on Bookabach. Lazy soak or races and ball games? Free time is up to you when your holiday property comes with a swimming pool.
What are popular home amenities in Old Saybrook?
Some of the most popular home amenities people are looking for in Old Saybrook include a garden, a fireplace and a nearby waterfront. Whether you're on the road with family, pals or even pets, Bookabach holiday homes include the best amenities for beginning new traditions with the people you love.
Are there large group holiday homes in Old Saybrook?
With four holiday homes that can sleep 10 or more guests in Old Saybrook, there's no need to keep your invite list short. From fun family get-togethers to special events like birthday and Christmas parties, Bookabach can help you find a large group home that fits the occasion.
Are there holiday homes in Old Saybrook that welcome kids?
Old Saybrook has 34 family-friendly holiday homes to pick from. And securing a stay that welcomes kids is a cinch with our "Properties good for families" filter. Besides having the whole place to yourselves, you'll get conveniences and perks such as living rooms, kitchens and pools.
What are the top attractions for families in Old Saybrook?
There's a ton of awesome things to see and do with the family in Old Saybrook, such as:

  • Essex Steam Train
  • Harveys Beach
  • Clinton Town Beach

Can I find two-bedroom holiday homes in Old Saybrook?
Old Saybrook has five two-bedroom properties for you to pick from. Go for a holiday home with all the space and privacy you're looking for at a price that's hard to resist on Bookabach.
Are there holiday homes with WiFi in Old Saybrook?
Old Saybrook has 19 holiday homes with WiFi, so you can stay connected when you're away. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with your family to posting pics on social media, these Bookabach homes make it easy to go online.
How can I find holiday homes with air conditioning in Old Saybrook?
Pick your travel dates and then make use of the filters to locate holiday homes with air conditioning in Old Saybrook on Bookabach. With 30 air-conditioned properties on offer here, you can look forward to a comfortable and cool stay.
How old do you have to be to rent a holiday home in Old Saybrook?
The minimum age is generally 16, 18 or 21. It can differ across properties on Bookabach, so check the rules of your chosen Old Saybrook stay before booking your stay.
How long can I rent a holiday home in Old Saybrook for?
The amount of time you can stay in an Old Saybrook holiday home for is down to the property. Just put in your preferred travel dates to browse options that offer extended stays. They come with all you require to make your extended getaway more convenient and enjoyable, such as air conditioning and kitchens. Some holiday homes may also offer weekly or monthly discounts, so you can have a longer stay for less.