Old Saybrook holiday homes

We found 431 holiday rentals — enter your dates for availability

Select from 56 homes, 22 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:19 Dec - 26 Dec
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Why visit Old Saybrook

  • Scenic waterfront: Stroll along the picturesque waterfront and soak in the stunning views of the Connecticut River.
  • Historic district: Discover the rich heritage of Old Saybrook by exploring its charming historic district.
  • Outdoor adventures: Enjoy a range of outdoor activities, from beach outings to hiking in nearby parks.
  • Local attractions: Visit the local railway museum and attractions at Saybrook Point for a taste of local culture.
  • Family-friendly vibe: Experience the welcoming atmosphere with friendly locals, making it perfect for families.

Top attractions in and around Old Saybrook

Old Saybrook, Connecticut, is perfect for a romantic getaway or outdoor adventure, boasting stunning beaches and picturesque scenery. Explore its historic charm along the Connecticut River, visit the local railway museum, or enjoy the attractions at Saybrook Point. Whether you're after culture or a relaxing day by the sea, Old Saybrook offers a delightful mix of experiences for every traveller.

  • Harvey's Beach: A quintessential beach experience right in Old Saybrook, Harvey's Beach offers a relaxing atmosphere with soft sands and gentle waves, perfect for sunbathing and swimming.
  • Harkness Memorial State Park: Located 22.5km away, this stunning park boasts picturesque scenery, abundant outdoor activities, and nature trails, ideal for adventure seekers and families alike.
  • Clinton Town Beach: Just 12.9km from Old Saybrook, Clinton Town Beach features a charming coastal vibe, making it a delightful spot for beachgoers to enjoy the sun and surf.

Things to do recommended for couples

For a romantic getaway in Old Saybrook, explore Kontokosta Winery for a delightful wine tasting, enjoy a meal at Anna Mia's for a charming dining experience, and have some fun at Shelter Island Whale's Tail mini-golf for a bit of adventure together.

Things to do recommended for families

Families visiting Old Saybrook can enjoy a fun day at Stay and Play LLC, an exciting arcade adventure zone. For some relaxation, head to Devil’s Hopyard State Park, just a short drive away, or take a dip at Ocean Beach Park, perfect for some family outdoor fun.

Things to do recommended for groups

Groups visiting Old Saybrook can enjoy shopping at Clinton Crossing Premium Outlets, just a short drive away, or explore the charming Essex Saybrook Antique Village. For a touch of culture, catch a performance at the Ivoryton Playhouse, where entertainment and family vibes abound.

*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

If you’re planning a trip with a group, family, pets, or looking for extended stays, it's important to refine your search based on your key preferences. Here are some helpful booking tips for using Vrbo.

  • Traveling to Old Saybrook with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group get-togethers. Thankfully, you can easily narrow down your options for all of this and more on Vrbo.
  • Traveling to Old Saybrook with young kids: Taking a trip with young kids can be quite demanding. It's important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, thinking about how close you are to family-friendly activities is a wise move.
  • Taking your pets with you to Old Saybrook: For many, a family holiday isn’t truly complete without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Old Saybrook: If you're in search of holiday rentals offering special rates for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to consider adding amenities like a parking space, a well-equipped kitchen, or a private pool to your search criteria.

Where to stay in and around Old Saybrook

Old Saybrook, a charming coastal town, offers a delightful mix of historical charm and scenic beauty, perfect for a relaxing getaway. Explore its historic district, where you can soak in the town's rich heritage. With family-friendly vibes and friendly locals, you'll feel right at home. Don't miss the chance to wander the picturesque waterfront and enjoy outdoor adventures, making your visit to this quaint town truly memorable.

  • Westbrook: Westbrook is a charming coastal town, located 6.4km from Old Saybrook, renowned for its stunning outdoor scenery and romantic ambiance. Visitors are drawn to its beautiful beaches, where you can relax or partake in water sports. The town is home to a variety of resorts and recreational areas, making it an ideal spot for families and couples alike. Music concerts and events often take place here, providing a vibrant cultural experience. Don't miss the chance to explore local landmarks, such as the picturesque family beach and event conference venues that enhance the town’s appeal.
  • Old Lyme: Situated a mere 4.8km from Old Saybrook, Old Lyme is a picturesque town celebrated for its outdoor adventures and scenic beauty. Nature lovers will find plenty to enjoy, from pristine beaches to the expansive national state park. The recreational areas offer activities like hiking and bird watching, perfect for those looking to explore the great outdoors. The local music scene and resorts add to the allure, making it a wonderful destination for both relaxation and adventure. Be sure to visit the family beach, where you can create lasting memories in a beautiful setting.
  • Old Saybrook Center: Nestled in the heart of Old Saybrook, Old Saybrook Center is a delightful neighbourhood known for its outdoor activities and breathtaking scenery. This area provides ample opportunities for skiing and recreational pursuits, making it a year-round destination for adventure seekers. With its close proximity to stunning beaches, serene lakes, and the national state park, visitors can immerse themselves in nature. Whether you’re skiing in winter or enjoying summer activities, Old Saybrook Center offers a perfect blend of excitement and relaxation amidst picturesque surroundings.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

Are you keen to save on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. You can also enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, make use of our filters to sort by price, location, and type of accommodation. Happy travels.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient area where you can plan new trips, keep your existing plans on track, or manage your bookings effectively. The properties you've saved or reserved are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply head over to: 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:

  • Chamard Vineyards (8.7 mi / 14 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)
  • Sannino's Bella Vita Vineyard (18 mi / 29 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)
  • 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.

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