Top Old Saybrook Hotel Deals

Make the Most of Your Old Saybrook Stay

A refined coastal gateway

Old Saybrook occupies a distinctive position where the Connecticut River meets Long Island Sound at a point fortified since 1635. The town's architectural character reflects its aristocratic past, particularly in the exclusive Fenwick borough, where Shingle-style summer cottages built for Connecticut's elite still line the streets. The Saybrook Breakwater Light, an 1886 cast-iron lighthouse featured on state license plates, marks the harbor entrance and defines the town's maritime identity. This is where Yale University began before relocating to New Haven, and where Katharine Hepburn found her refuge from Hollywood.

Cultural sophistication and waterfront dining

The Katharine Hepburn Cultural Arts Center anchors Main Street's cultural offerings in a restored 1911 Colonial Revival town hall, presenting theater, music, and film alongside exhibits of the actress's personal collection. Saybrook Point Resort serves as the town's premier destination, where Fresh Salt restaurant delivers farm-to-table cuisine with marina views. The dining scene balances upscale waterfront establishments with approachable Main Street venues, while the General William Hart House provides insight into 18th-century merchant life.

Strategic positioning for exploration

Amtrak's Northeast Regional service connects Old Saybrook directly to Boston and New York, while Shore Line East provides commuter access throughout the Connecticut coast. The town serves as an ideal base for exploring nearby Essex's maritime museums, Mystic's seaport attractions, and Gillette Castle. Members can apply miles toward accommodations at waterfront properties.

Frequently Asked Questions about Old Saybrook

Can I book hotels in Old Saybrook with miles on Delta Stays?

Yes, you can use your Delta miles for your hotel reservation in Old Saybrook, or you can opt for a miles-plus-cash combination to provide more booking options. Upon accessing your Delta SkyMiles® account, you will find Member-valued offers at participating properties that could enhance your visit.

What are the benefits of booking my Old Saybrook hotel on Delta Stays?

As a SkyMiles Member, you will earn 2 miles per $1 you spend on completed hotel stays and vacation rentals booked through Delta Stays. You will also enjoy access to special Member offers at select properties, and have the flexibility to pay with miles, cash, or a combination of both. To receive your miles, make sure to log in to your SkyMiles account or provide your SkyMiles number during checkout when making a cash payment. Please allow up to 8 weeks after completing a stay for miles to appear in the SkyMiles account provided. Please also note that if you use miles to pay for any portion of your stay, you will not earn miles on that reservation, including any amount paid with cash.

Can I change or cancel my hotel booking made through Delta Stays?

Each property maintains its own cancellation policy. We suggest reviewing the cancellation policies displayed in the detailed information for each hotel before completing your reservation. Some rates are refundable, while others are non-refundable. Any modifications or cancellations to your reservation may affect the number of miles you earn and receive in your account.

Can I book with my Delta SkyMiles® American Express® Card?

As a Delta SkyMiles® Gold, Platinum, or Reserve American Express® Cardholder, you can earn additional miles along with valuable benefits, including an annual statement credit of up to $200 applicable toward prepaid accommodations booked through Delta Cars and Stays. These offers are subject to specific terms. Learn more about your benefits at the Delta SkyMiles® American Express Credit Cards page.

Can I earn MQDs on Delta Stays hotel bookings?

From time to time, Delta Stays may present special opportunities for SkyMiles Members to earn Medallion® Qualification Dollars on their hotel and vacation rental bookings made through Delta Stays. We recommend accessing the Delta Stays MQD Offer page to view current MQDs promotions and examine their terms and conditions.

Do I need to be a Delta SkyMiles Member to book a hotel on Delta Stays?

No, Delta Stays is available to everyone for hotel bookings. However, by becoming a SkyMiles Member, you will unlock the ability to earn miles and access Member-only prices and offers. As a Member, you will earn 2 miles per $1 you spend on Delta Cars and Stays (excluding taxes and additional charges). Plus joining SkyMiles is free. Visit the delta.com to join today.

Can I book a vacation rental through Delta Stays?

Yes, beyond traditional hotels, Delta Stays provides an extensive collection of vacation rentals for your travel needs. You have access to numerous homes, condos, and specialty lodging options powered by Vrbo to suit your travel preferences. You can discover these alternative accommodations by visiting the Vacation Rentals page.

Which hotels have high ratings in Old Saybrook?

In Old Saybrook, you’ll find 8 hotels to choose from when you book on Delta Stays. Saybrook Point Resort & Marina has a guest rating of 9.6 out of 10, and features 2 outdoor pools and a full-service spa. Another top-rated bed & breakfast is James Pharmacy Bed & Breakfast, where you can enjoy a free local cuisine breakfast and free parking.

Which area in Old Saybrook should I book for my stay?

Old Saybrook is home to a wide variety of fascinating neighborhoods loved by travelers and locals.

Old Saybrook Center captures classic New England charm along its walkable Main Street, where historic buildings house local boutiques and fresh seafood restaurants. The Kate, a 285-seat theater honoring Katharine Hepburn, anchors the cultural scene. One of the popular places to stay in the area is James Pharmacy Bed & Breakfast.

What's a good time of year to visit Old Saybrook?

To experience Old Saybrook during great weather, visit in July when temperatures average 77°F with sunny skies and warm seas ideal for water activities. For off-peak prices and fewer crowds, consider April or October when temperatures reach 55-65°F with pleasant conditions and lodging rates up to 20% lower.

What hotels in Old Saybrook are near Katharine Hepburn Cultural Arts Center?

The Kate honors Katharine Hepburn with intimate performances in a 285-seat theater. Arrive early to explore the free museum showcasing the actress's costumes and memorabilia. One popular hotel is James Pharmacy Bed & Breakfast which is steps away. Madison Beach Hotel is another well-reviewed hotel and it is within a short drive.

What hotels in Old Saybrook are located closest to Saybrook Country Barn?

This historic 1799 building houses 42,000 square feet of premium furniture and designer apparel across multiple showrooms, with the on-site Aspen Restaurant for a break. One popular hotel is James Pharmacy Bed & Breakfast which is steps away. Another hotel is Madison Beach Hotel and it is within a short drive.

What hotels in Old Saybrook are near Chalker Beach?

This private shoreline community has welcomed families since 1931, offering soft sands, gentle waves, and summer concerts that create an intimate coastal atmosphere along Connecticut's coast. Popular hotels include James Pharmacy Bed & Breakfast which is a short drive away. Another top hotel is Madison Beach Hotel and it is within a short drive.

*Terms and conditions:

Mileage Offer:

SkyMiles Members will earn two (2) miles per US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Opens in a new window on the base hotel rate for a completed hotel stay. Base hotel rate is the cost of the hotel room, before taxes and fees, charged at the time of booking or upon checkout. Taxes and fees, gratuities, room service other booking charges, or any bookings which are paid or reduced by miles, redemption vouchers or discount codes are excluded from mileage credit. For clarity, if miles are used as a form of payment (whether for all or a portion of the booking), no portion of the booking will be eligible to earn miles under this offer. Except with respect to the Hertz Mileage offer (listed below), SkyMiles Members will earn two (2) miles per eligible US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Cars on the base car rental rate for a completed car qualifying rental booking (“Qualifying Dollars”). A qualifying rental booking includes rentals at a participating location for one or more days at rates other than travel industry rates or discounts, wholesale of tour package rates or discounts, wholesale tour package rates, insurance/dealer replacement rates, corporate and government rates, group travel discounts, or rentals in conjunction with a frequent flyer car award, or other corporate agreements applicable to the respective car company. Calculation of the applicable standard mileage offer is listed below by car rental company. Qualifying Dollars include the base car rental rate, which is the cost of the car rental before taxes and fees, charged at the time of booking. Taxes, fees, other incidental charges, or other booking charges or any bookings which are paid or reduced by redemption vouchers or discount codes are excluded from mileage credit and are not included in the Qualifying Dollars.

This mileage offer does not apply to stays or car rentals booked through Delta Vacations or any cruises booked through Delta Cruises.

Standard mileage offer for car rentals booked at https://www.delta.com/Opens in a new window or https://carsandstays.delta.com/Opens in a new window:

Hertz Reservations:

• General SkyMiles Members earn 4 miles per Qualifying Dollar

• Silver Medallions earn 5 miles per Qualifying Dollar

• Gold Medallions earn 6 miles per Qualifying Dollar

• Platinum Medallions earn 7 miles per Qualifying Dollar

• Diamond Medallions earn 8 miles per Qualifying Dollar

Dollar and Thrifty Reservations:

• All SkyMiles Members earn 4 miles per Qualifying Dollar

Alamo, Enterprise, National, Avis, Budget, Payless and SIXT Reservations:

• All SkyMiles Members earn 2 miles per Qualifying Dollar