Old Saybrook Vacation Packages
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Your Old Saybrook Vacation
From its rich history to its coastal scenery and beyond, there's much to like about Old Saybrook. Uncover the wonders of this interesting city with a Old Saybrook vacation package that's tailor-made for you. You'll want to do a little exploring during your trip to Old Saybrook. Find time for famous attractions like Essex Steam Train, Harveys Beach and Westbrook Town Beach. Whoever you're going away with and whatever your budget, your dream Old Saybrook vacation is just a few clicks away with Expedia.
Top Old Saybrook Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Landing Apartments New Haven Near Dixwell
Newhallville
CA $1,489
per person
Sep 17 - Sep 20
found 4 hours ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.
Reviewed on May 25, 2026
Hyatus Luxury Residences City Crossing
The Hill
CA $1,186
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.4/10 Exceptional! (33 reviews)
Everything about the property & staff was AMAZING! Zero complaints, would 100% stay there again if in the area. Thank you!
Reviewed on Jul 24, 2026
Old Saybrook Beach Vacation
Shake off the stresses of daily life and let your body, mind and soul unwind on your Old Saybrook vacation. There's nothing more refreshing than the salty sea air and the sound of waves lapping at the shore. Plan your trip to Old Saybrook the easy way by choosing one of our Old Saybrook vacation deals. Many visitors choose to stay near Chalker Beach, a local highlight only 3 kilometres from the downtown area.
Things You Should Know About Old Saybrook
- Choose one of our Old Saybrook beach hotels to enjoy the very best this destination has to offer. Wander along the water's edge and be inspired by the stunning sunrises right on your front door.
- Our private vacation homes, like Saybrook Point Resort & Marina and Super 8 by Wyndham Old Saybrook, are popular with travellers of all sorts. Check out the facilities and get set for your stay in Old Saybrook!
- Head to our Old Saybrook things to do page for some trip planning inspiration. With a population of roughly 26,924 cm Old Saybrook, we're sure there'll be a few locals who'll be pleased to give you some extra advice!
- If you're searching for things to do while you're in town, add Hammonasset Beach State Park, Hammonasset Beach State Park and Clinton Crossing Premium Outlets to your travel itinerary. Also, take a look at our Old Saybrook vacation deals to get great deals on your hotels and experiences.
Ready to book your vacation to Old Saybrook?
Old Saybrook Hotel Deals
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
CA $137
CA $157 total
Aug 10 - Aug 11
includes taxes & fees
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
Fully refundableReserve now, pay when you stay
CA $514
CA $640 total
Sep 3 - Sep 4
includes taxes & fees
9.6/10 Exceptional! (1,006 reviews)
"Great place. Great staff"
Reviewed on Aug 8, 2026
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
Fully refundable
CA $141
CA $162 total
Aug 30 - Aug 31
includes taxes & fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Old Saybrook attractions
Harvey's Beach
8.8/10 (93 reviews)
If a restful vacation is part of your travel plans, Harvey's Beach might be the perfect place to seek out during your trip to Old Saybrook. Visit the shops and spas in this relaxing area.
Chalker Beach
8.8/10 (26 reviews)
Why not spend a lazy afternoon at Chalker Beach during your trip to Old Saybrook? Stroll along the area's beaches or simply enjoy its restaurants.
Katharine Hepburn Cultural Arts Center
8.8/10 (53 reviews)
Enjoy an outing to Katharine Hepburn Cultural Arts Center during your stay in Old Saybrook. While you're in the area, stroll along the beautiful beaches.
Essex Saybrook Antique Village Shopping Center
9.0/10 (66 reviews)
You can find the perfect gifts to bring home at Essex Saybrook Antique Village Shopping Center during your stay in Old Saybrook. While you're in the area, stroll along the beautiful beaches.
Crystal Lake Town Park
8.4/10 (16 reviews)
Explore the great outdoors at Crystal Lake Town Park, a lovely green space in Old Saybrook. While you're in the area, stroll along the beautiful beaches.
Saybrook Country Barn
9.0/10 (27 reviews)
Enjoy an outing to Saybrook Country Barn during your stay in Old Saybrook. While you're in the area, stroll along the beautiful beaches.
General William Hart House
9.0/10 (17 reviews)
You can find out about the history of Old Saybrook with a stop at General William Hart House. While you're in the area, stroll along the beautiful beaches.
Fort Saybrook Monument Park
10.0/10 (1 review)
Find out about the history of Old Saybrook when you spend time at Fort Saybrook Monument Park.
Frequently asked questions
How much does an Old Saybrook vacation package cost?
Offering excellent value package deals from CA $771 on Expedia, you'll be pleasantly surprised at how much a vacation to Old Saybrook costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Old Saybrook?
If you're looking to score a cheap Old Saybrook vacation package, consider planning a trip in January, March and April. You're likely to find better rates on flights and hotels during these months — perfect for travellers wishing to save money.
How many days is enough for Old Saybrook?
Dedicate at least 2 days for your Old Saybrook vacation to really immerse yourself in everything that makes this place unique. Stroll around popular areas, including Saybrook Manor and Old Saybrook Centre. Then head to the top sights like Essex Saybrook Antique Village Shopping Centre and Essex Library. With a well-planned itinerary, you'll be kept busy with room for some relaxation too. Want to travel outside of Old Saybrook? Consider fitting in an excursion or two.
Is it worth booking a vacation package to Old Saybrook?
Whether you're planning to check out attractions such as Tanger Outlets and Katharine Hepburn Cultural Arts Centre, or eager to experience its top-notch dining and culture, an Old Saybrook vacation is sure to exceed your expectations. Book your trip with Expedia and discover why Old Saybrook is such a good vacation destination.
How to find the best Old Saybrook package deals?
Landing a cheap Old Saybrook package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Old Saybrook package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book an Old Saybrook vacation as a package?
An Expedia vacation package could land you great savings when compared to booking flights and hotels separately. Better still, you can personalize your Old Saybrook trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Old Saybrook?
Land amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Old Saybrook getaway.
How to plan a trip to Old Saybrook?
- Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Old Saybrook.
- Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to activities and flights. Your accommodations will probably be the largest expense during your trip to Old Saybrook.
- Set the duration of your trip: Start by listing all the attractions and activities you'd like to get to in Old Saybrook. Then, estimate how long you'll need for each, including any travel time.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find an Old Saybrook vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
