Old Saybrook Vacations from $400

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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.

The Latest Old Saybrook vacation packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $539, price is now $400 per person
$400
per person
Oct 1 - Oct 4
found 15 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)
Lage room, Clean and comfortable bed. Bathroom could use updating and an elevated toilet seat. Staff very nice. Would stay again.

Reviewed on Jul 7, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $1,009, price is now $731 per person
$731
per person
Oct 1 - Oct 4
found 15 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) 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

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $1,010, price is now $750 per person
$750
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
9.2/10 Wonderful! (1,005 reviews)
steps out front and no parking, but clean

Reviewed on Jul 3, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,769, price is now $1,343 per person
$1,343
per person
Sep 9 - Sep 13
found 15 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
No reviews

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $680, price is now $530 per person
$530
per person
Oct 1 - Oct 4
found 15 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to New Haven (HVN)
8.8/10 Excellent! (1,084 reviews)
We may become a repeat quest.

Reviewed on Jul 7, 2026

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Stay near popular Old Saybrook attractions

A wooden boardwalk leading to a beach at sunset.

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.
See properties

Old Saybrook Hotel Deals

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $108 total per night from Jul 12 to Jul 13
$108 total
Jul 12 - Jul 13
Total with taxes and fees
8/10 Very Good! (1,009 reviews)
"Lage room, Clean and comfortable bed. Bathroom could use updating and an elevated toilet seat. Staff very nice. Would stay again."

Reviewed on Jul 7, 2026

Pier Blue Inn Old Saybrook - Essex
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St Old Saybrook CT
$393 nightly
The price is $453 total per night from Jul 21 to Jul 22
$453 total
Jul 21 - Jul 22
Total with taxes and fees
9.6/10 Exceptional! (1,007 reviews)
"Very clean and updated room. Mattress and pillows were very comfortable. Nice furnishings and a large TV. The outdoor pool is not that big so you must get there before 8am to get a lounge. It was great to have a spa on site. My massage therapist was excellent. The check in was painless and the staff ..."

Reviewed on Jul 6, 2026

Saybrook Point Resort & Marina
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd Old Saybrook CT
$118 nightly
The price is $136 total per night from Jul 29 to Jul 30
$136 total
Jul 29 - Jul 30
Total with taxes and fees
7.8/10 Good! (1,001 reviews)
"Good stay accommodating, Staff"

Reviewed on Jun 30, 2026

Quality Inn Old Saybrook - Westbrook
See all 2,932 properties in Old Saybrook
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.

Find the Best Old Saybrook Vacation Packages

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 2 miles 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 travelers 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 in 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.

Old Saybrook Essential Information

Language
English
Currency
U.S dollars
Population
10,600
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Harveys Beach, Goodspeed Opera House and Connecticut River Museum

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Frequently asked questions

How much does an Old Saybrook vacation package cost?
You can pick up a vacation package to this destination from $400 on Expedia. But how much your vacation 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?
December, January and February are great times to search for cheap Old Saybrook vacation packages. Traveling in less busy periods means you can generally find lower prices on accommodations and flights.
How many days is enough for Old Saybrook?
With around 2 days, you'll have enough time to enjoy popular neighborhoods such as Old Saybrook Center and Saybrook Manor during your Old Saybrook vacation. Make sure to also add Stay and Play LLC and Crystal Lake Town Park to your sightseeing list. In the mood for more adventures? Consider exploring outside of Old Saybrook on tours and day trips.
Is it worth booking a vacation package to Old Saybrook?
Whether you're planning to discover attractions such as Harvey's Beach and Tanger Outlets, or want to experience its top-notch dining and culture, an Old Saybrook vacation is sure to exceed your expectations. Book your getaway with Expedia and find out why Old Saybrook is such a good vacation destination.
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 vacation as a package?
An Expedia vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Old Saybrook vacation packages?
Your Old Saybrook getaway should be an escape from your busy life, not a source of money worries. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.