Old Saybrook Vacations from $338

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $421, price is now $338 per person
$338
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.2/10 Wonderful! (861 reviews)
A very stylish hotel. Quiet.

Reviewed on Aug 21, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $563, price is now $447 per person
$447
per person
Nov 7 - Nov 10
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,007 reviews)
It would’ve been better that you had posted that the pool was closed since 2020. My Wife wasn’t too happy about that.

Reviewed on Aug 18, 2025

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $761, price is now $636 per person
$636
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.4/10 Exceptional! (312 reviews)
The hotel is beautiful and the grounds are wonderful. The staff was top notch. We will definitely stay again.

Reviewed on Aug 18, 2025

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $709, price is now $594 per person
$594
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.4/10 Exceptional! (19 reviews)
Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay.

Reviewed on Jun 27, 2025

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $1,007, price is now $857 per person
$857
per person
Oct 9 - Oct 14
found 18 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.4/10 Very Good! (1,000 reviews)
Staff and property were great. The pool was out of service for our stay so that wasn’t great. The location was excellent for what we were doing in Connecticut. It is walkable to some dining places and they have snacks and beverages on hand for purchase. Very convenient.

Reviewed on Aug 18, 2025

Don't see what you're looking for?
See all available trips from Columbus to Old Saybrook
View all trips

Discover the most popular places to visit in Old Saybrook

Harvey's Beach

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.

Harvey's Beach

Katharine Hepburn Cultural Arts Center

You can enjoy a show at Katharine Hepburn Cultural Arts Center during your trip to Old Saybrook. While you're in the area, stroll along the beautiful beaches.

Katharine Hepburn Cultural Arts Center

Essex Saybrook Antique Village Shopping Center

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.

Essex Saybrook Antique Village Shopping Center

Old Saybrook Hotel Deals

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
$419 nightly
The price is $479 total per night from Aug 26 to Aug 27
$479 total
Aug 26 - Aug 27
Total with taxes and fees
9.4/10 Exceptional! (1,007 reviews)
"The venue is great."

Reviewed on Aug 20, 2025

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
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Sep 15 to Sep 16
$116 total
Sep 15 - Sep 16
Total with taxes and fees
7.6/10 Good! (1,011 reviews)
"Perfect spot for my visit"

Reviewed on Aug 17, 2025

Quality Inn Old Saybrook - Westbrook
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
$88 nightly
The price is $102 total per night from Sep 7 to Sep 8
$102 total
Sep 7 - Sep 8
Total with taxes and fees
7.8/10 Good! (1,005 reviews)
"The staff was excellent. Very friendly and accommodating. And the room was comfortable and clean."

Reviewed on Aug 21, 2025

Pier Blue Inn Old Saybrook - Essex
See all 2,820 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.

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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Old Saybrook vacation package cost?
You can pick up a vacation package to this destination from $338 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.