Old Saybrook vacation rentals

We found 485 vacation rentals — enter your dates for availability

Select from 50 homes, 23 cottages, and other vacation rentals in Old Saybrook to find one that's perfect for your trip. Whether you’re staying in a vacation home with your kids and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include WiFi and a pool. Whatever you're looking for, you'll be able to choose a rental that has what everyone needs, including accessible or non-smoking choices.

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Find out more about Old Saybrook

Why visit Old Saybrook

  • Stunning Beaches: Enjoy the beautiful Connecticut shoreline, perfect for sunbathing and beach activities.
  • Outdoor Adventures: Explore local State Parks for hiking, biking, and nature walks.
  • Historic Sites: Visit the iconic Old Saybrook Point and learn about the town's rich history.
  • Family-Friendly Activities: Engage in various activities that cater to all ages in a welcoming atmosphere.
  • Charming Accommodations: Find unique vacation rentals, from cozy cottages to spacious homes by the beach.

Popular types of accommodation in Old Saybrook

When it comes to vacation rentals in Old Saybrook, Vrbo offers a variety of options to suit your needs. From charming cottages and spacious private homes to cozy apartments, you'll find the perfect place to unwind. Whether you're searching for beach rentals close to the shore or a tranquil house rental for your family getaway, Old Saybrook has something for everyone. Explore your options and make the most of your stay in this beautiful coastal town.

  • Houses: The top choice for visitors in Old Saybrook, offering spacious and comfortable living, perfect for families or groups.
  • Cottages: Quaint and charming, these rentals provide a cozy atmosphere, ideal for a peaceful getaway.
  • Apartments: A convenient option for those seeking a modern stay with easy access to local attractions.
  • Condos: Stylish and well-equipped, these accommodations offer a blend of comfort and luxury.
  • Villas: Luxurious and spacious, perfect for travelers wanting an upscale experience in Old Saybrook.**

Top attractions in and around Old Saybrook

Old Saybrook, Connecticut, is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can enjoy stunning beaches, explore the local State Parks, and discover the fascinating railway museum. With a blend of natural beauty and cultural attractions, Old Saybrook offers a memorable experience for those looking to immerse themselves in outdoor adventures and beach relaxation.

  • Essex Steam Train: Experience the nostalgia of a bygone era as you ride on this historic railway. Located 4 miles from Old Saybrook, the Essex Steam Train offers a unique glimpse into the culture and charm of steam-powered travel, complete with scenic views of the Connecticut River.
  • Harvey's Beach: Enjoy a relaxing day at Harvey's Beach, located within Old Saybrook. This picturesque beach features soft sands and inviting waters, perfect for sunbathing, swimming, and family picnics, all surrounded by a friendly, laid-back atmosphere.
  • Hammonasset Beach State Park: Located 10 miles away, this expansive state park offers adventure and stunning scenery. With miles of sandy beaches, nature trails, and picnic areas, it's an ideal spot for outdoor enthusiasts looking to explore and unwind in nature.

Things to do recommended for couples

For a romantic getaway in Old Saybrook, visit Kontokosta Winery for a cozy evening, enjoy a meal at Anna Mia's for delightful dining, and add some fun at Shelter Island Whale's Tail mini-golf. Each spot offers unique vibes perfect for couples looking to create memorable moments.

Things to do recommended for families

During your family vacation in Old Saybrook, enjoy a refreshing day at Ocean Beach Park, only 14 miles away, or explore the excitement at Stay and Play LLC, right in town. For some outdoor fun, visit Devil’s Hopyard State Park, just 5 miles away, perfect for relaxation and wellness.

Things to do recommended for groups

In Old Saybrook, your group can shop at Clinton Crossing Premium Outlets for a mix of entertainment and city vibes, explore unique finds at Essex Saybrook Antique Village, and enjoy a captivating performance at the Ivoryton Playhouse, just a short drive away, embracing culture and family fun.

*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 traveling with a group, family, or pets, or if you're planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Old Saybrook with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Old Saybrook with young kids: Traveling with little ones can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities 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 trip isn't truly complete without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and cozy beds to ensure that everyone feels at home.
  • Planning for a long term stay visiting Old Saybrook: If you're in search of vacation rentals that offer discounts for stays of a month or longer, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider including features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Old Saybrook

Old Saybrook, Connecticut, offers a charming blend of history and natural beauty, making it an ideal destination for outdoor and romantic getaways. Explore the picturesque Connecticut shoreline, visit the historic Old Saybrook Point, and enjoy family-friendly activities in the welcoming atmosphere. With its relaxing scenery and vibrant local culture, Old Saybrook promises a delightful city break that captures the essence of New England charm.

  • Westbrook: Located 4 miles from Old Saybrook, Westbrook is a picturesque coastal town known for its stunning outdoor scenery and romantic ambiance. This charming city offers a variety of activities, including visits to local resorts and music concerts that enhance the travel experience. Nature lovers can enjoy the nearby beaches and family-friendly recreational areas, making it an ideal destination for relaxation and fun. Don't miss the opportunity to explore local landmarks and events that further enrich your stay in this vibrant community.
  • Old Lyme: Just 3 miles from Old Saybrook, Old Lyme is a haven for outdoor enthusiasts and adventure seekers. This historic town is renowned for its captivating scenery and recreational opportunities, such as hiking and beach outings. Visitors can partake in music concerts and enjoy the local resort atmosphere while exploring the nearby national state park. The combination of beautiful beaches and lush landscapes makes Old Lyme a perfect spot for those looking to immerse themselves in nature and art.
  • Old Saybrook Center: Nestled within Old Saybrook, Old Saybrook Center offers a delightful blend of outdoor adventure and scenic beauty. This quaint neighborhood is perfect for those seeking recreational activities like skiing in the winter and enjoying the nearby lake and national state park during warmer months. With its charming atmosphere, visitors can explore local attractions including beaches that promise relaxation and fun. Old Saybrook Center is an excellent choice for travelers looking to experience the unique charm of Connecticut's coastal life.

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. Peak season runs from June to August, while off-peak times, like January to March tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.3°F (-0.4°C)Light RainMostly SunnyLowModerately Low
February32.4°F (0.2°C)Light RainMostly SunnyLowModerately Low
March38.5°F (3.6°C)Light RainMostly SunnyLowModerately Low
April48.2°F (9.0°C)Light RainMostly SunnyAverageAverage
May57.9°F (14.4°C)Light RainMostly SunnyAverageAverage
June66.4°F (19.1°C)Light RainMostly SunnyHighModerately High
July73.8°F (23.2°C)Light RainMostly SunnyHighModerately High
August72.7°F (22.6°C)Light RainMostly SunnyHighModerately High
September66.2°F (19.0°C)Light RainMostly SunnyAverageAverage
October56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
November45.5°F (7.5°C)Light RainMostly SunnyAverageAverage
December37.8°F (3.2°C)Light RainMostly SunnyAverageAverage

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices can fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to narrow down your options by price, location, and type of vacation rental. We’re here to help you find the perfect getaway.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you’ll receive OneKeyCash on the full booking amount. Being the trip organizer certainly has its perks. Enroll in our One Key rewards program to unlock exclusive member discounts and earn OneKeyCash on qualifying stays. Sign up today and begin enjoying the benefits.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly space to plan new trips, continue from where you last stopped, or manage your travel arrangements. You'll find your saved or booked properties neatly organized into categories: Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Travel to beautiful Old Saybrook

Enjoy the history and other features of Old Saybrook. This city is scenic and relaxing, recognized for its beaches, golfing and shopping. If you're looking for accommodations with space to entertain friends and family, Vrbo 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

Are you hoping to find top things to see and do in the area? Venture out of your cozy vacation rental and experience everything that makes Old Saybrook a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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)
  • RJ Julia Booksellers (11.4 mi / 18.3 km)

Exploring the beaches and other natural features in Old Saybrook

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Old Saybrook is a great place to spend some time outside. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city center:

  • Harvey's Beach (1.9 mi / 3 km)
  • Goose Island (3.1 mi / 4.9 km)
  • Westbrook Town Beach (4.3 mi / 7 km)
  • Clinton Town Beach (7.7 mi / 12.3 km)
  • Attawan Beach (9 mi / 14.4 km)
  • McCook Point Beach (9.3 mi / 15 km)

Seasonal weather averages in Old Saybrook

If you're planning a vacation around warm-weather activities, July, August, June and September are the hottest months to visit, when temperatures average 70°F.

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 center. If you can't find a flight that's convenient for your trip, you could book a flight to Fishers Island, NY (FID-Elizabeth Field), which is 18.3 mi (29.4 km) away.

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

Frequently asked questions

What is the best area to stay in Old Saybrook, Connecticut, United States of America when booking a vacation rental?
When considering a vacation rental in Old Saybrook, Connecticut, the area around the waterfront is particularly appealing. This charming coastal town offers a blend of scenic beauty and historical significance, making it a delightful spot for a getaway. Here, you'll find a variety of quaint properties, many of which boast stunning views of the Connecticut River and Long Island Sound.

Staying near the waterfront allows easy access to the picturesque Saybrook Point, where visitors can enjoy lovely walking paths and watch boats come and go. The nearby Old Saybrook Historical Society Museum is another attraction worth exploring, providing insights into the town's rich heritage.

In addition, the vibrant downtown area features boutique shops, delightful cafes, and restaurants offering fresh seafood and local cuisine.
How much does it cost to rent a vacation home in Old Saybrook?
Prices for vacation 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 vacation 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, travelers should focus on the picturesque waterfront areas along Long Island Sound. The shoreline near the Old Saybrook Town Beach is particularly appealing, offering easy access to sandy shores and scenic views. Beach houses in this area often feature amenities such as large decks, outdoor seating areas, and well-equipped kitchens, superb for enjoying family meals with a view.

Another top area is near the Saybrook Point, where visitors can find charming homes with private docks, making it ideal for those interested in boating or fishing. Many of these properties come with modern conveniences like air conditioning, Wi-Fi, and outdoor grills for summer barbecues.

Additionally, the vicinity of the Old Saybrook Lighthouse provides a unique backdrop, with some rentals offering direct beach access, cozy fire pits, and spacious living areas for relaxation after a day of sun and sand. The area is also close to local shops and restaurants, enhancing the overall experience for vacationers looking to explore the local culture and cuisine.
What is the most popular type of vacation rental accomodation in Old Saybrook?
In Old Saybrook, vacation houses are the most popular rental option, with about 38 available throughout the area. These houses often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families and larger groups. Many properties also include outdoor patios or decks, great for enjoying the coastal breeze after a day of exploring the nearby beaches and parks. Additionally, there are around 18 charming cottages that provide a cozy, intimate atmosphere. These cottages typically come with kitchen facilities and comfortable living spaces, offering a quaint retreat close to the scenic Connecticut River and Long Island Sound.
Are there any family house rentals in Old Saybrook?
In Old Saybrook, Connecticut, there are plenty of family-friendly rental options available—around 42 homes to choose from. This charming coastal town offers a variety of properties, many located near the picturesque waterfront and scenic parks. Visitors can expect spacious living areas, fully equipped kitchens for convenient meal preparation, and comfortable bedrooms that cater to families.

Many of these homes also feature outdoor spaces, superb for barbecues or relaxing in the fresh air, and some may even include amenities like game rooms or play areas for children.

The town is conveniently situated near attractions such as the Old Saybrook Lighthouse and the beautiful beaches along the Connecticut shoreline, making it an excellent base for exploring the area.
Can I rent a vacation home with a pool or hot tub in Old Saybrook?
In Old Saybrook, there are several vacation homes available for rent that come equipped with pools and hot tubs. This charming coastal town provides a wonderful setting for a relaxing getaway, with properties often located near the picturesque waterfront or located in serene neighborhoods. Travelers can expect amenities such as private swimming pools, hot tubs for unwinding after a long day, spacious outdoor decks, and fully equipped kitchens, making these homes great for families or groups looking for comfort and enjoyment.
Can I find long-stay vacation rentals in Old Saybrook?
A long-stay vacation rental in Old Saybrook is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Old Saybrook?
In Old Saybrook, travelers can find a variety of pet-friendly house rentals, with around 17 options available. Many of these homes are situated close to the scenic Connecticut shoreline, providing easy access to beaches and parks where pets are welcome. Expect amenities such as spacious yards, outdoor seating areas, and fully equipped kitchens, making it convenient for families or groups traveling with pets.

The area around the Old Saybrook town center offers charming vacation rentals that are great for enjoying the local attractions, including nearby beaches like Harvey's Beach and the picturesque Saybrook Point. In addition, the nearby Preserve State Forest features walking trails that are great for leisurely strolls with pets. See all pet-friendly rentals in Old Saybrook.
Are there any remote work vacation rentals in Old Saybrook?
In Old Saybrook, Connecticut, there are plenty of remote work-friendly vacation rentals available, with around 53 options to choose from. Many of these properties are equipped with essential amenities for remote work, such as high-speed Wi-Fi and comfortable workspaces. Travelers can expect spacious living areas that allow for both productivity and relaxation, as well as fully equipped kitchens for convenient meal preparation.

The town itself is charming, situated at the mouth of the Connecticut River and offering beautiful coastal views. You can explore nearby attractions like the historic Saybrook Point, as well as local shops and restaurants that enhance the experience of working remotely in a picturesque setting. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Old Saybrook vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Old Saybrook with parking available—perfect for families or travelers 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 vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals and enjoy dining in comfort. Many rentals also feature outdoor spaces such as decks or patios, great for relaxing or entertaining while taking in the scenic views of the surrounding area. Onsite parking is commonly available, making it convenient for visitors with vehicles. Additional amenities often include blenders for making smoothies or cocktails, enhancing the vacation experience.
When is the best time to visit Old Saybrook for a vacation rental?
The most popular time to visit Old Saybrook is during the summer months, specifically from June to August. This vibrant peak season draws visitors eager to enjoy the beautiful beaches, scenic coastal views, and a variety of outdoor activities. With warm temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, it's an ideal time for swimming, sailing, and exploring the charming town.

July, in particular, stands out as the busiest month, bustling with tourists and offering a lively option. This is when you can partake in local events, enjoy fresh seafood at waterfront restaurants, and soak up the sun along the shoreline. Families and adventure seekers alike will find plenty to keep them engaged, from hiking in nearby parks to relaxing on the beach.

If you're seeking a more budget-friendly option, consider planning your visit in November. This month offers a quieter experience, allowing you to appreciate the serene beauty of Old Saybrook as the fall foliage begins to fade. You can enjoy leisurely strolls along the coast and explore local shops without the summer crowds.

Ultimately, the best time for you to book a vacation rental in Old Saybrook hinges on your preference for vibrant summer activities or a more tranquil fall getaway.
How early should I book a Old Saybrook vacation rental?
Book your Old Saybrook vacation 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 vacation 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, Connecticut, United States of America?
In Old Saybrook, visitors can explore several attractions that highlight the town's coastal charm and rich history. The Old Saybrook Point, where the Connecticut River meets Long Island Sound, offers picturesque views and is a great spot for leisurely walks. Nearby, the historic Goodspeed Opera House in East Haddam is renowned for its musical productions and is a short drive away.

For those interested in local history, the Katherine Hepburn Cultural Arts Center, honoring the famous actress who spent much of her life here, hosts various performances and exhibitions. The town's scenic beaches, such as Harvey's Beach, provide opportunities for sunbathing and water activities. Additionally, the Old Saybrook Lighthouse, known as the Saybrook Breakwater Lighthouse, is a must-see for its historic significance and beautiful backdrop for photographs.

Nature enthusiasts can enjoy the nearby Hammonasset Beach State Park, just a short drive away, where trails, picnic areas, and stunning coastal scenery await.
Can I change or cancel my Old Saybrook home rental booking on Vrbo?
To find Old Saybrook vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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