Old Saybrook Vacation Packages 2026 from $344

Old Saybrook flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Best Western Executive Hotel Of New Haven - West Haven

$344

per person

Jun 3 - Jun 7

found 1 day ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Omni New Haven Hotel at Yale

Downtown New Haven

Save 100% on your flight

$759

per person

Jun 3 - Jun 7

found 1 day ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.

Madison Beach Hotel

Madison Center

Save 100% on your flight

$1,677

per person

Jun 11 - Jun 15

found 14 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the gym and perks like free WiFi.

Graduate by Hilton New Haven

Downtown New Haven

Save 100% on your flight

$693

per person

Jun 3 - Jun 7

found 1 day ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.

Landing Furnished Apartment Near Yale University

Downtown New Haven

Save 100% on your flight

$469

per person

Jun 3 - Jun 7

found 1 day ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

A gym is featured at this apartment, along with free WiFi in public areas and laundry facilities. A virtual front desk are provided for your convenience.

Top Old Saybrook hotels deals

Saybrook Point Resort & Marina

2 Bridge St Old Saybrook CT

Free Cancellation

Reserve now, pay when you stay

$325 nightly

$374 total

Mar 26 - Mar 27

Total with taxes and fees

A full-service spa, a marina, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and free train station pick-up. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and a shopping center shuttle.

Pool

Hot Tub

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

$80 nightly

$92 total

Mar 30 - Mar 31

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area and barbecue grills are also provided.

Pet friendly

Parking included

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$113 total

Mar 29 - Mar 30

Total with taxes and fees

Pool

Breakfast included

New Haven Hotel

229 George Street New Haven CT

Free Cancellation

Reserve now, pay when you stay

$92 nightly

$106 total

Mar 31 - Apr 1

Total with taxes and fees

A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Pet friendly

Free WiFi

Hyatt Place Uncasville - Casino Area

2049 Norwich Montville CT

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$108 total

Apr 15 - Apr 16

Total with taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

Pool

Breakfast included

Mohegan Sun

1 Mohegan Sun Boulevard Montville CT

Get rates

This luxury resort features a golf course, a casino, and a full-service spa. Families will appreciate the arcade/game room, onsite laundry facilities, and babysitting. Enjoy a meal in one of the 19 restaurants and free perks like valet parking and a casino shuttle.

Pool

Hot Tub

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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.

Popular places to visit

Harvey's Beach

4.5/5(3 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.

The sun sets on the final days of summer over a beach

Chalker Beach

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

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.

Frequently asked questions

How much are vacation packages to Old Saybrook?

Packages, which include flights and hotels in Old Saybrook, are priced from as little as $344. Turn your travel fantasies into reality and begin your booking with Travelocity today.

How long should my Old Saybrook vacation be?

If you need some guidance, most visitors spend approximately 2 nights vacationing in Old Saybrook. But to discover the true spirit of this destination, stay a few extra days. You'll be able to explore more and really experience the local culture.

Where can I get the best vacation package deals for Old Saybrook?

With around 400 air carriers and 1,000,000 hotels across the world, it's hard to go past Travelocity. Make the most of our comprehensive range and score an incredible Old Saybrook vacation package. Isn't it great when traveling is that easy?

Why should I book my Old Saybrook vacation bundle with Travelocity?

Because we believe in creating special travel experiences. From flights and hotels to car rentals and activities, our packages make traveling a breeze. Our support team is available 24/7 to make sure your needs are taken care of. We also offer a Price Match Guarantee, so you can lock in your vacation knowing you've landed the best deal possible. How? If you find a lower price, we'll match it!

Will I save money on my Old Saybrook car rental if I bundle it with a hotel or flight?

With an Old Saybrook vacation package, you can combine your car, hotel and flight bookings and save a ton. If you're eager to uncover the best of this fabulous location, why not head to Times Square? This well-known sight is 90 mi from Old Saybrook. With your own set of wheels, you'll be there in a jiffy.

Which airport is best for Old Saybrook?

There's a high chance you'll be landing at Bradley Intl. Airport (BDL), situated 45 mi north of inner Old Saybrook. T.F. Green Airport (PVD) (55 mi away from central Old Saybrook) and MacArthur Airport (ISP) (50 mi away from central Old Saybrook) are other options.

What is there to do in Old Saybrook?

There is an undeniable magic as you wander through the streets of Old Saybrook. Katharine Hepburn Cultural Arts Center and Chalker Beach are just a couple of landmarks that make this city so special, so put them on your travel itinerary.

Where should I stay when visiting Old Saybrook?

If you're searching for a place to spend your nights, check out the Quality Inn Old Saybrook - Westbrook. It's the top choice for many travelers.

Where to stay in Old Saybrook: Best areas for travelers

Westbrook: Featuring Westbrook Town Beach, this is a fantastic place to immerse yourself in the coastal life. Want to go from your bed to the beach fast? Book a room in the area. The Waterfront Cottage on Long Island Sound With Awesome Salt Island out Front, Water's Edge Resort & Spa and the July 19-26, 2019 Water\'s Edge Resort and SPA in CT. Special Price $1,200/week are some attractive options.
Westbrook Center: Westbrook Town Beach is just one of the numerous interesting sights to take in here. If you spend your evenings at a well-positioned place like the Waterfront Cottage on Long Island Sound With Awesome Salt Island out Front, the Water's Edge Resort & Spa or the July 19-26, 2019 Water\'s Edge Resort and SPA in CT. Special Price $1,200/week, you'll really be able to discover all that this neighborhood has to offer.
Madison: For a comfortable place to spend your nights, look up the Madison Beach Hotel and the Madison, CT. You'll soon understand why travelers keep coming back to this area and these hotel options.
Clinton: Scattered around this neighborhood are some of the city's most popular attractions. Check in to the Clinton Motel, the Spa Like Oceanside Home. Get Your 2019 Early Booking Discounts now or the Lamplighter Motel - Clinton, Connecticut and you won't be too far away from Clinton Crossing Premium Outlets. For an unforgettable trip, make sure Clinton Plaza Shopping Center and Indian River Marina are part of your itinerary too.
Saybrook Manor: There are tons of things to see and do in this city, but this area is an attraction in its own right. The Pier Blue Inn Old Saybrook - Essex and the Family Friendly, Newly Renovated Cottage - Chalker Beach are a few places from which to discover this sought-after neighborhood.