Old Saybrook Holidays
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Old Saybrook Beach Holiday
Shake off the stresses of daily life and let your body, mind and soul unwind on your Old Saybrook holiday. 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 holiday 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 holiday 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 10,600 inches 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 holiday deals to get great deals on your hotels and experiences.
Top hotels in Old Saybrook
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
S$144
10 Aug - 11 Aug
includes taxes & fees
8/10 Very good! (1,002 reviews)
"Very dated and no elevator. Room was very hot when we got there."
Reviewed on 9 Aug, 2026
Saybrook Point Resort & Marina
2 Bridge St Old Saybrook CT
Fully refundableReserve now, pay when you stay
S$571
3 Sept - 4 Sept
includes taxes & fees
Quality Inn Old Saybrook - Westbrook
100 Essex Rd Old Saybrook CT
Fully refundable
S$149
30 Aug - 31 Aug
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)
Harvey's Beach offers pristine white sand and calm, shallow waters perfect for families with young children. Explore the expansive sandbars at low tide to discover fascinating tide pools and marine treasures.
Chalker Beach
8.8/10 (26 reviews)
This private Connecticut shoreline offers a tranquil escape with soft sands and gentle waves. Generations of families have created a close-knit beach community here since 1931, complete with summer concerts and bonfires.
Katharine Hepburn Cultural Arts Center
8.8/10 (53 reviews)
The Kate honours Katharine Hepburn's legacy through intimate performances in Old Saybrook. Enjoy theatre productions, then explore the museum's collection of the iconic actress's costumes and memorabilia.
Essex Saybrook Antique Village Shopping Center
9.0/10 (66 reviews)
Discover treasures spanning decades at this 6,000-square-foot antique haven with over 50 dealers. Browse art glass, nautical artefacts, and vintage furniture while knowledgeable staff share the stories behind each piece.
Crystal Lake Town Park
8.4/10 (16 reviews)
This 180-acre recreational haven features trails, sports fields, and Crystal Lake for fishing. Hike through scenic woodlands or gather with family at the pavilion overlooking tranquil waters.
Saybrook Country Barn
9.0/10 (27 reviews)
Housed in a historic 1799 building, Saybrook Home offers 42,000 square feet of premium furniture and designer apparel. Browse multiple showrooms of quality home décor before dining at the on-site Aspen Restaurant.
General William Hart House
9.0/10 (17 reviews)
Step into the 1767 Georgian residence of Revolutionary War General William Hart, with its distinctive eight corner fireplaces. Guided tours reveal colonial life through period furnishings and family stories.
Fort Saybrook Monument Park
10.0/10 (1 review)
Explore Connecticut's first military fortification from 1635 at this historic waterfront park. Follow the elevated boardwalk for panoramic river views and discover colonial history through informative storyboards.
Frequently asked questions
How much does an Old Saybrook holiday package cost?
You can pick up a holiday package to this destination on Expedia. But how much your holiday to Old Saybrook costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Old Saybrook?
You're likely to find lower rates and greater availability in January, March and April. Take a look at our cheap Old Saybrook holiday packages and you could get some great off-season discounts.
How many days is enough for Old Saybrook?
With around 2 days, you'll have plenty of time to experience popular neighbourhoods like Saybrook Manor and Old Saybrook Centre during your Old Saybrook holiday. Remember to also add Harvey's Beach and Crystal Lake Town Park to your sightseeing list. Looking for more adventures? Consider exploring outside of Old Saybrook on tours and day trips.
Is it worth booking a holiday package to Old Saybrook?
Well known for its dining, culture and a host of other highlights, you can be certain Old Saybrook is a good holiday destination. Some of the top attractions to add to your itinerary? Check out Tanger Outlets and Katharine Hepburn Cultural Arts Centre during your Old Saybrook holiday.
How to find the best Old Saybrook package deals?
Start your search for an Old Saybrook package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Old Saybrook package deal straight away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Old Saybrook getaway off to a flying start.
Is it cheaper to book an Old Saybrook holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Old Saybrook trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Old Saybrook?
If you're planning a spur-of-the-moment Old Saybrook getaway, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Old Saybrook?
- Choose when to travel: Check your diary and get your bags packed. Your favourite season and the activities available will also help you decide when to escape to Old Saybrook.
- Plan your budget wisely: As well as the price of your hotel, you'll need to factor in other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Old Saybrook.
- Decide how long to go for: Now that you know more about Old Saybrook, you can work out the perfect length of your break. Create a rough plan and allocate enough time to get through everything on your must-do list.
- Combine your accommodation and airfare: Once you've settled on your trip dates and duration, lock in the perfect Old Saybrook holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
