Airbnb Management
Full-service Airbnb management for your short-term rental. Nationwide.
Old Saybrook, Connecticut
In Old Saybrook, Connecticut, guests can find a variety of Airbnb accommodations that cater to diverse preferences and needs. The options range from charming coastal cottages and historic homes to modern apartments and cozy guest suites. Many of these properties offer picturesque views of the Long Island Sound or are nestled in serene, wooded areas, providing a tranquil retreat. Some Airbnbs are located near the town center, offering easy access to local shops, restaurants, and cultural attractions, while others are more secluded, ideal for those seeking privacy and relaxation. Additionally, guests can find unique stays such as converted barns or vintage-style homes, each offering a distinct experience reflective of the area's rich history and coastal charm.
In Old Saybrook, Connecticut, there are currently no specific local laws governing the operation of Airbnbs or short-term rentals. However, hosts must comply with state regulations and general zoning laws that may affect rental properties. Connecticut requires Airbnb hosts to collect and remit a 15% occupancy tax, which includes a 6% state sales tax and a 9% room occupancy tax. Hosts are responsible for ensuring their properties meet safety and health standards, and they should be aware of any homeowner association rules or lease agreements that might restrict short-term rentals. Additionally, hosts should stay informed about any potential changes in local regulations as municipalities across the state continue to evaluate the impact of short-term rentals on their communities.
Managing an Airbnb in Old Saybrook, Connecticut, involves several key tasks to ensure a smooth operation and positive guest experience. Hosts need to focus on maintaining the property, which includes regular cleaning, restocking essentials, and ensuring all amenities are in working order. Effective communication with guests is crucial, from promptly responding to inquiries and booking requests to providing detailed check-in instructions and local recommendations. Pricing strategies should be regularly reviewed to remain competitive, taking into account seasonal demand and local events. Additionally, compliance with local regulations and tax requirements is essential to avoid any legal issues. Implementing a system for collecting and responding to guest feedback can help improve the service and maintain high ratings.
Old Saybrook, Connecticut, offers a charming coastal experience with several great areas to consider for an Airbnb stay. The Saybrook Point area is ideal for those seeking picturesque views and proximity to the waterfront, with easy access to the Saybrook Point Resort & Marina and scenic walks along the Connecticut River. The town center, or Main Street area, provides a quaint New England vibe with its historic architecture, boutique shops, and local dining options, making it perfect for visitors who enjoy exploring on foot. For a more serene and nature-focused experience, the Fenwick neighborhood offers beautiful landscapes and is close to the Fenwick Golf Course and Harvey's Beach, providing a peaceful retreat with opportunities for outdoor activities. Each of these areas offers a unique taste of Old Saybrook's coastal charm and hospitality.
Old Saybrook, Connecticut, presents a promising market for Airbnb investment due to its charming coastal appeal and historical significance. Nestled along the Long Island Sound, this picturesque town attracts visitors year-round with its beautiful beaches, quaint downtown area, and rich cultural heritage, including the Katharine Hepburn Cultural Arts Center. The town's proximity to major urban centers like New York City and Boston makes it an attractive weekend getaway, enhancing its rental demand. Additionally, Old Saybrook's blend of upscale homes and cozy cottages provides diverse investment opportunities, catering to both luxury travelers and budget-conscious visitors. The town's strong community vibe and local attractions, such as the Saybrook Point Resort & Marina, further bolster its appeal as a desirable Airbnb destination.
As of the latest data, the average Airbnb revenue for properties in Old Saybrook, Connecticut, reflects a moderate yet promising market for short-term rentals. This coastal town, known for its charming New England atmosphere and proximity to the Long Island Sound, attracts a steady stream of visitors, particularly during the summer months. Hosts in Old Saybrook typically see higher occupancy rates and increased revenue during peak tourist seasons, with many properties benefiting from the town's appeal as a vacation destination. While the average revenue can vary significantly based on factors such as property size, location, and amenities offered, hosts generally find that well-maintained and strategically marketed listings can achieve competitive earnings in this picturesque region.
Old Saybrook, Connecticut, experiences a moderate occupancy rate for Airbnbs, with notable fluctuations due to its seasonal appeal. The town's coastal location and charming New England atmosphere make it particularly popular during the summer months, when tourists flock to enjoy the beaches, boating, and local attractions. As a result, occupancy rates tend to peak from June through August. In contrast, the winter months see a decline in visitors, leading to lower occupancy rates, although some travelers are drawn to the area's serene winter landscapes and holiday events. Spring and fall offer a more balanced occupancy, as visitors come to enjoy the mild weather and seasonal activities such as leaf-peeping and local festivals. Overall, Old Saybrook's Airbnb market is characterized by its strong summer demand and quieter off-season periods.
Why Choose Checkmate Rentals?
![]() | Other Property Managers | |
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Cost | Starting at 15% fee | 25-40% fee |
Guest Communications | Guest response within 10 minutes, 24 hours a day | Sporadic guest communications |
Host Communications | Designated host call in phone line | Bot response assistants |
Insurance | Full damage protection for every reservation | Unreliable insurance coverage |
Contract | No annual agreements | Contract lock-ins |
Checkmate Rentals

Attract Guests
List on top booking sites
Optimize listings for SEO
Feature show-stopping photos
Competitive, dynamic pricing
Mangage Operations
Tailored pricing algorithms
24/7 guest service
Reliable, professional cleaning
Restocking & inventory management
Maintenance coordination


Host Care
Unlimited owner stays
Flexible contract options
East to use host portal
Set it and forget it billing
Exclusive insurance discounts via our partner network
Get in touch with us.

Checkmate Rentals is a full-service property manager. That means the Airbnb listing, the home, the guest and the work is our responsibility.
Local Team Support
Know that you have a friendly, accessible team right up the road to handle any property needs.
Guest Screenings
Book only the most qualified guests 25 and over who’ll enjoy your home the right way.
Unlimited Owner Use
Block off your vacation days with ease, and enjoy your home as often as you want.
Reliable Property Maintenance
Keep your home running smoothly around the clock with a fast, reliable maintenance team.
Transparent Finances
Transparent Finances Booking payouts get paid directly to you for full financial transparency. We never handle your money.
Fast 24/7 Guest Communication
Make every guest feel cared for with industry best response times of 1-15 minutes day and night.
Marketing
Target, attract & book qualified guests with photography, email marketing, and optimized listings.
Revenue Management
Get the competitive edge with dynamic pricing and rates optimized daily by your pricing manager.

Ready to make the jump?
Let's get started! Schedule a call today to learn more about Checkmate Rentals.