Old Saybrook holiday lettings

We found 508 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

Image gallery for Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Pool
10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient

8% off
Price is £9,632
for 7 nights, 1 room
£1,376 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

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Why visit Old Saybrook

  • Scenic Beaches: Enjoy the picturesque Connecticut shoreline, perfect for relaxing walks and sunbathing.
  • Historic Landmarks: Discover the rich history of Old Saybrook through its charming historic sites and the Old Saybrook Centre.
  • Tranquil Parks: Explore beautiful urban parks that offer serene spaces for picnics and leisurely strolls.
  • Saybrook Point: Experience the tranquil beauty of Saybrook Point, ideal for waterfront activities and community events.
  • Cozy Accommodations: Choose from a variety of charming vacation rentals, including cottages and private homes, for a delightful stay.

Popular types of accommodation in Old Saybrook

Welcome to Old Saybrook, Connecticut, a charming coastal town rich in history and natural beauty. Here, you can explore picturesque beaches, historic landmarks, and scenic parks. Popular accommodation options include houses, cosy cottages, and comfortable apartments, ensuring a delightful stay. Whether you're seeking a serene retreat or an adventurous getaway, Old Saybrook's vacation rentals provide the perfect base to discover its unique attractions and experiences.

  • Houses: The top choice for visitors in Old Saybrook, offering spacious and comfortable living for families and groups.
  • Cottages: Quaint and charming, these provide a perfect escape for a peaceful retreat amidst nature.
  • Apartments: Conveniently located, apartments offer a home-like atmosphere ideal for short or extended stays.
  • Condos: A popular option for those seeking modern amenities and community facilities.
  • Villas: Luxurious and spacious, villas are perfect for a lavish getaway with stunning views.**

Top attractions in and around Old Saybrook

Old Saybrook, Connecticut, offers a charming seaside escape perfect for outdoor enthusiasts and romantics alike. Explore the scenic beaches, visit urban parks, and experience the tranquil beauty of Saybrook Point. Enjoy leisurely strolls along the waterfront or engage in local meetups to immerse yourself in the community's culture. Whether you're seeking relaxation or adventure, Old Saybrook promises a delightful getaway for all types of travellers.

  • Harvey's Beach: A serene beach located within Old Saybrook, offering a relaxed atmosphere perfect for sunbathing and swimming. Its gentle waves and sandy shores make it an ideal spot for families and relaxation.
  • Hammonasset Beach State Park: A stunning state park renowned for its scenic views and outdoor adventures, featuring miles of coastline perfect for hiking, picnicking, and wildlife watching.
  • Orient Point County Park: A family-friendly urban park that combines city vibes with outdoor activities, offering playgrounds, picnic areas, and trails for leisurely walks amidst natural beauty.

Things to do recommended for couples

For a romantic getaway in Old Saybrook, explore the quaint waterfront and share a sunset picnic at Saybrook Point. Enjoy a leisurely stroll along the beach, or indulge in a candlelit dinner at a charming local restaurant, where exquisite cuisine complements the intimate atmosphere.

Things to do recommended for families

Families visiting Old Saybrook can enjoy a delightful day at the renowned Saybrook Point Park, perfect for picnics and nature walks. Children will love the fun activities at the nearby Childrens Museum of Southeastern Connecticut, where learning meets play in a captivating environment.

Things to do recommended for groups

Groups visiting Old Saybrook can experience the thrill of motor racing at Waterford Speedbowl, located 21km away. This venue offers an exhilarating atmosphere perfect for those seeking adventure and excitement in the heart of Connecticut.

*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 travelling with a group, family, or pets, or if you're considering extended stays, it's important to apply the right filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Old Saybrook with a group: Think about how many bedrooms you require, along with features like a fully-equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Old Saybrook with young kids: Travelling with young children can present some challenges. It's important to prioritise their comfort and safety, as well as access to suitable amenities like a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Old Saybrook: For many, a family holiday wouldn’t feel whole without their furry companion by their side. If this resonates with you, explore Vrbo accommodations that welcome pets. Most of these pet-friendly properties come equipped with feeding bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Old Saybrook: If you’re seeking holiday rentals with discounts 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 rentals. Don’t forget to include preferences such as 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 destination perfect for a relaxing getaway. Explore the scenic Connecticut shoreline, where you can enjoy picturesque views and tranquil walks. The historic Old Saybrook Centre offers a glimpse into the town's rich past, while the inviting atmosphere of South Cove is ideal for family-friendly excursions. Don't miss the chance to unwind by a fireplace and soak in the romantic vibes that this delightful city has to offer.

  • Westbrook: Located a mere 6km from Old Saybrook, Westbrook is a charming coastal town renowned for its stunning outdoor scenery and romantic settings. Visitors can indulge in a variety of activities, from relaxing at local resorts to enjoying live music concerts. The beautiful beaches, including family-friendly options, provide the perfect backdrop for a day of sun and sand. Westbrook also boasts excellent golf courses and event venues, making it an ideal spot for both leisure and special occasions.
  • Old Lyme: Just 5km away from Old Saybrook, Old Lyme offers a delightful mix of outdoor adventure and scenic beauty. This quaint town is a haven for nature lovers, with its picturesque landscapes and recreational areas perfect for hiking and mini golf. Families can enjoy the sandy shores of nearby beaches, while the nearby national state park invites exploration and discovery. Old Lyme's tranquil atmosphere makes it a perfect destination for those seeking relaxation amidst nature's splendour.
  • Greenport: Situated 21km from Old Saybrook, Greenport is a delightful beach town that combines outdoor activities with a romantic coastal vibe. Here, visitors can explore beautiful beaches and parks while enjoying the area's vibrant recreational offerings, including golf courses and music concerts. Greenport's laid-back charm and stunning waterfront views make it an ideal spot for leisurely strolls and sunset watching, providing a perfect escape for those looking to unwind by the sea.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 simple

Are you eager to save on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a dedicated area for you to plan new trips, manage ongoing arrangements, or review and organise your bookings. Your saved or booked properties are conveniently categorised into Potential, Upcoming, or Current Trips. To explore the Trip Boards, please visit: https://www.vrbo.com/en-gb/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 best area to stay in Old Saybrook when booking a holiday rental?
When considering the best area to stay in Old Saybrook, Connecticut, you might want to explore the charming neighbourhoods that offer a delightful blend of coastal beauty and local attractions. One particularly appealing area is along the waterfront, where you can find a variety of holiday rentals that provide stunning views of the Long Island Sound. This picturesque setting not only allows for easy access to the beach but also places you near the iconic Old Saybrook Lighthouse, a lovely spot for a leisurely stroll and superb for capturing memorable photographs.

Another excellent option is the historic district, which is characterised by its quaint New England architecture and a friendly setting. Here, you'll find a number of properties that showcase the area's rich maritime heritage. This neighbourhood is conveniently located near the Katharine Hepburn Cultural Arts Centre, where you can enjoy a range of performances and events that celebrate the arts.

Overall, Old Saybrook has a diverse selection of properties available for holiday rentals, suiting various tastes and preferences.
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, the area around the Old Saybrook Lighthouse and the stunning waterfront along Long Island Sound is highly recommended. This picturesque coastal town offers a variety of holiday rentals, many of which are situated just steps from the beach, providing breathtaking views of the water. Properties in this area typically come with amenities such as spacious decks for outdoor dining, modern kitchens, and cozy living areas, superb for families or groups looking to enjoy beachside relaxation.

The charming neighbourhood of Saybrook Point is particularly appealing, as it features homes that often have private access to the beach and may include additional luxuries like hot tubs and fire pits for evening gatherings. Nearby, the Old Saybrook Historical Society and the Katharine Hepburn Cultural Arts Centre offer cultural experiences for visitors, enhancing the overall appeal of the area.

Additionally, the scenic waterfront parks, such as Harvey's Beach, provide opportunities for swimming, picnicking, and beachcombing, making it a great spot for those seeking a mix of leisure and outdoor activities. Rentals in this region frequently offer added conveniences like outdoor showers, laundry facilities, and proximity to local shops and restaurants, ensuring a comfortable and enjoyable stay for beachgoers.
What is the most popular type of holiday rental accomodation in Old Saybrook?
In Old Saybrook, holiday houses are the predominant type of holiday rental, with around 152 available throughout the area. These spacious properties are typically situated in serene neighbourhoods, making them ideal for families or groups seeking a relaxing getaway. Most holiday houses come equipped with multiple bedrooms, fully furnished kitchens, and comfortable living areas, along with outdoor spaces such as decks or gardens for enjoying the pleasant Connecticut weather. Additionally, there are about 72 charming cottages scattered around the town, offering a cozier alternative with similar amenities, superb for couples or smaller families.
Are there any family house rentals in Old Saybrook?
In Old Saybrook, Connecticut, there is a wide selection of family-friendly homes available, with approximately 42 properties scattered throughout the area. This charming coastal town offers a superb blend of relaxation and adventure for families. Many of these homes boast spacious living areas, fully equipped kitchens, and outdoor spaces ideal for children to play. Visitors can also expect amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.

The neighbourhoods around the Old Saybrook town centre offer easy access to beautiful beaches, including the popular Harvey's Beach, where families can enjoy sunbathing and swimming. Additionally, the nearby Saybrook Point Park provides opportunities for picnicking, walking trails, and stunning views of the Connecticut River. For those interested in history, the Old Saybrook Historical Society and the General William Hart House are also within reach, adding to the richness of the area.
Can I rent a holiday home with a pool or hot tub in Old Saybrook?
In Old Saybrook, there are several holiday homes available for rent that feature either pools or hot tubs. This picturesque coastal town, located at the confluence of the Connecticut River and Long Island Sound, offers a charming setting for travellers. Many of these properties can be found in residential neighbourhoods, providing a peaceful retreat while still being close to local attractions.

Rentals often come equipped with amenities such as private swimming pools, hot tubs, spacious outdoor areas superb for gatherings, and fully equipped kitchens for self-catering. Some properties might also include features like barbecue grills and beautifully landscaped gardens, enhancing the experience of outdoor living.
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 several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these properties come equipped with amenities such as spacious yards, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups looking to enjoy a home away from home.

The area is known for its charming coastal scenery and offers easy access to various parks and outdoor spaces where pets can enjoy walks and playtime. Nearby, the Old Saybrook Town Park features beautiful green spaces and walking trails, superb for leisurely strolls with your furry companions. Additionally, the scenic views along the Connecticut River provide a lovely backdrop for outdoor activities.
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 212 available throughout the area. This charming coastal town offers a variety of properties that cater to those needing a conducive work environment. Many rentals provide essential amenities such as free Wi-Fi, allowing for seamless connectivity while you work.

Properties often feature comfortable living spaces with dedicated work areas, ensuring a productive atmosphere. Additionally, many homes come equipped with full kitchens, allowing you to prepare meals during your stay. The scenic surroundings of Old Saybrook, with its picturesque beaches and quaint downtown, provide a lovely backdrop for unwinding after a day of work.

Moreover, you can explore local attractions such as the historic Saybrook Point and the scenic views along the Connecticut River, making this destination ideal for both work and leisure. 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 rental amenities cater to a comfortable and convenient stay. Most holiday rentals feature kitchens, allowing guests to prepare their own meals and enjoy the local produce. Many properties also include inviting decks or patios, superb for relaxing outdoors and soaking in the charming coastal atmosphere. Onsite parking is commonly available, making it easy for travellers with vehicles to explore the area. Additionally, some rentals offer blenders, ideal for whipping up refreshing smoothies or cocktails during a relaxing getaway.
When is the best time to visit Old Saybrook for a holiday rental?
The best time to book a holiday rental in Old Saybrook is during the peak season from June to August. This delightful period invites families and beach enthusiasts to relish the sunny weather and enjoy the picturesque coastline of Connecticut. July stands out as the most popular month, where vibrant activities abound, from beach outings to local festivals that bring the community together.

During these summer months, you can expect warm temperatures, typically ranging from 20 to 30 degrees Celsius, making it ideal for outdoor adventures such as kayaking on the Connecticut River or simply soaking up the sun on the sandy beaches. The lively option is complemented by a variety of dining options and quaint shops, ensuring that every moment is filled with enjoyment.

For those seeking a more budget-friendly option, consider visiting in November. While it's outside the busy tourist season, this month offers a tranquil experience where you can explore the charming town without the crowds. The fall foliage creates a beautiful backdrop for leisurely strolls along the waterfront.

Ultimately, your choice of when to visit Old Saybrook will depend on whether you prefer the energetic summer vibe or the peaceful charm of the off-peak season.
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 discover a blend of natural beauty and historical charm. The Old Saybrook Lighthouse, also known as Saybrook Breakwater Lighthouse, is a picturesque landmark that offers stunning views of the Long Island Sound. The nearby Saybrook Point Park and Marina provides a lovely space for leisurely walks, picnics, and enjoying waterfront activities.

Additionally, the town boasts the historic Goodspeed Opera House, renowned for its productions and picturesque riverside location. For those interested in nature, the nearby Cockaponset State Forest offers hiking trails and opportunities for wildlife viewing. The charming downtown area features quaint shops and restaurants, making it a delightful spot to explore local culture.
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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