We are open May 6th - October 8th 2022. Please book directly with us via our website! We look forward to welcoming you at our beautiful place on Cape Cod.
Looking for a charming getaway on Cape Cod? A Little Inn on Pleasant Bay offers cozy rooms, water views, and European-inspired hospitality. With only nine rooms, this boutique inn delivers a personalized experience, complete with a historic setting, private dock, and award-winning service. From kayaking to relaxing in English gardens, the inn blends comfort with adventure.
Here’s what you need to know:
Whether you're visiting for the vibrant summer or the peaceful shoulder seasons, this guide ensures a stress-free stay at one of Cape Cod's most celebrated inns.
A Little Inn on Pleasant Bay provides an array of thoughtful amenities designed to make your Cape Cod getaway unforgettable. From charmingly designed guest rooms to exclusive access to the bay, every element of the inn showcases a perfect blend of New England charm and upscale comfort.
The inn’s rooms are a tribute to authentic New England style, capturing the essence of Cape Cod’s coastal beauty. Interior designer Matthew Yee has skillfully brought the outdoors in, using a palette inspired by the bay - navy, turquoise, coral, and seafoam.
"Interior designer Matthew Yee beautifully evokes the feeling of the Cape by expertly capturing hues of navy, turquoise, coral and seafoam." - Matthew Yee
Each room comes equipped with air conditioning, complimentary toiletries, plush bathrobes, hair dryers, and daily housekeeping. Many rooms also boast stunning views, whether of the sparkling bay or the inn’s meticulously maintained gardens. Accommodations range from cozy queen bedrooms to expansive king suites, many featuring special touches like cathedral ceilings, private balconies, or garden terraces. For instance, the Whistler room offers a balcony overlooking the English gardens and fountain, while the Knockabout room treats guests to breathtaking sunrise views over Pleasant Bay.
Beyond the private quarters, the inn’s shared spaces and outdoor areas invite guests to relax and connect with the natural beauty of their surroundings.
The inn’s outdoor amenities are designed to make every moment of your stay memorable. A private dock stretches into Pleasant Bay, where guests can take advantage of complimentary kayaks and paddle boards for a bit of adventure on the water. For a unique experience, the inn’s 21-foot boat is available for personalized water tours led by the owner.
"Great outdoor space: Plenty of different places to relax (including a small wooden dock out in the bay) and enjoy the beautiful views over Pleasant Pleasant Bay." - TarOwo, Tripadvisor Reviewer
The English gardens, complete with a charming fountain and pond, provide a tranquil setting for sipping your morning coffee or unwinding in the evening. Adirondack chairs scattered across patios offer the perfect spot to soak in the bay views. For those who enjoy the beach, a nearby rocky shoreline provides opportunities for swimming and fishing. When the weather turns cooler, the inn features two indoor common rooms where guests can relax in comfort.
To round out your experience, the inn offers concierge services for dining reservations, sightseeing tips, and help with planning special occasions. They also assist with tours and tickets, ensuring you make the most of your time on Cape Cod. If you’re arriving after 8:00 PM, simply contact the property in advance to arrange for a seamless check-in.
Now that we've covered the unique amenities, let's dive into how to pick the perfect room for your Cape Cod getaway. With nine distinct rooms at A Little Inn on Pleasant Bay, each offers features tailored to different preferences and travel styles.
Start by thinking about what matters most to you during your stay. For many guests, breathtaking views top the list. If that's your priority, consider water-view rooms like the Knockabout or Daysailer, where you can soak in stunning bay vistas right from your window.
Prefer a serene garden setting? Look for rooms with private balconies or terraces overlooking the inn’s lush gardens and fountains. These spots are perfect for savoring a peaceful morning coffee or unwinding in the evening.
If you're after something spacious or architecturally distinct, the Wianno room in the carriage house offers romantic artwork and cathedral ceilings for a cozy yet elegant feel. The Baybird, with its porthole windows and soaring ceilings, creates a light and airy atmosphere. For longer stays or special occasions, the Wilton Suite stands out with its two-room layout, including a separate sitting area.
Other factors to consider include proximity to shared spaces, noise levels, and specific amenities. For families or groups, the Sharpie room - with two double beds and direct lawn access - provides convenience and comfort. Meanwhile, the Beetlecat offers a spacious king bedroom with bay window views and modern touches that blend seamlessly with the inn's historic charm.
If you're unsure which room aligns with your plans, reach out to the inn's concierge. They can guide you in selecting a room that complements your activities, whether you're planning water adventures, garden relaxation, or exploring Cape Cod’s many attractions.
Once you’ve decided on your ideal room, timing is everything. With only a handful of accommodations available, early planning is essential - especially for peak summer months like July and August. For the best chance at securing a water-view room or one with private outdoor space, aim to book 6–8 months in advance.
Weekends tend to fill up faster than weekdays, so a midweek stay might offer more choices and flexibility. If your schedule allows, consider visiting in spring (April–June) or autumn (September–October). These seasons bring mild weather, fewer crowds, and more availability while still delivering the charm of Cape Cod.
Certain rooms, like the Wilton Suite, are particularly popular for special occasions and often require early reservations. Likewise, water-view rooms and those with private outdoor areas are always in high demand, so booking ahead is key.
For last-minute plans, flexibility is your best friend. Adjusting your dates or room preferences can help you snag a spot. No matter which room you choose, the inn's prime location at 654 South Orleans Road in Orleans ensures you'll have easy access to Cape Cod's attractions and activities.
Booking directly through the inn's website not only guarantees the best rates but also lets you make special requests. Plus, early reservations give you plenty of time to map out your itinerary. Once your room is secured, the concierge team is ready to help you plan everything from dining to local adventures, ensuring your Cape Cod escape is as seamless as possible.
Cape Cod's charm and popularity mean planning ahead is essential, especially during the busy summer months. Here's what you need to know about visiting and booking your stay during peak times.
The best time to experience Cape Cod is from early June through late October, when the weather is at its finest [4]. July and August are the busiest months, drawing crowds eager to soak up the summer vibe.
"Summer on the Cape is all about the beautiful beaches and amazing views, chill atmosphere, fantastic seafood, tons of entertainment with town band concerts, outdoor movies, and Cape Cod Baseball League games." - Amy Squeglia, owner of Peace, Love, Sup [4]
For a more peaceful getaway, consider visiting during the shoulder seasons - early May or late September through October. These months still feature pleasant weather but with far fewer crowds. From breathtaking sunrises over Pleasant Bay to exploring local attractions at your own pace, the Cape’s allure remains strong. A Little Inn on Pleasant Bay operates from May 6th to October 8th, making early May and late September ideal for those seeking mild temperatures and a quieter atmosphere.
Guests visiting during peak season can also take advantage of exclusive water activities from the inn’s private dock, adding a unique touch to summer stays.
Once you've decided on your travel dates, it’s important to understand the inn’s booking and cancellation policies to avoid surprises.
Cancellation policies are structured as follows:
Given the inn’s limited nine-room capacity and seasonal schedule, rooms fill up quickly during peak times. Early booking is key. Guests who meet the minimum stay requirements also enjoy complimentary harbor tours aboard "A Little Boat", offering an added perk for longer stays [5].
Planning ahead ensures you’ll have your spot secured to enjoy everything Cape Cod has to offer, whether it’s the lively summer energy or the calm of the shoulder seasons.
Make your Cape Cod getaway seamless by planning ahead with smart packing and clear transportation arrangements.
Cape Cod’s weather can be a bit unpredictable, so packing layers is key. Even in summer, evenings by the water can feel chilly, while spring and fall bring fluctuating temperatures. Be prepared for anything by packing versatile clothing.
Stick to casual, classic styles in nautical colors like navy, white, and neutral tones. Comfortable walking shoes are essential for exploring Orleans’ charming streets, while breathable fabrics will keep you cool on warm afternoons. Don’t forget a light jacket for evening walks along Pleasant Bay.
Planning to hit the beach? Pack sunscreen, swimwear, and a wide-brimmed hat for those sunny days. While the inn provides beach towels, you’ll want your own gear for trips to spots like Skaket Beach, just a 12-minute drive away [2][3].
A reusable water bottle is a must for staying hydrated during your adventures. Toss in a small first-aid kit with essentials like band-aids, pain relievers, and aloe vera for minor scrapes or sunburns. Checking the weather forecast a few days before your trip can help you fine-tune your packing list, especially during the spring and fall when the weather can change quickly.
Once you’ve packed, it’s time to plan your arrival and how you’ll get around.
A Little Inn on Pleasant Bay is located at 654 South Orleans Road in Orleans, making it an easy destination from Boston and nearby areas [2][5][1]. If you’re flying, Logan International Airport is about a 108-minute drive from the inn [2][3].
Traveling from Boston offers several options. Buses tend to be more budget-friendly, while the Cape Flyer train provides a more comfortable ride and accommodates bikes and luggage [7][8]. If you’re planning to explore multiple Cape Cod towns, renting a car is the most convenient choice. However, renting a car directly at Logan Airport can be pricey due to MassPort fees, so consider booking at an off-site location instead [8].
If you’ll be arriving after 8:00 PM, make sure to inform the inn ahead of time. This allows the staff to coordinate your check-in and ensure a smooth arrival [2][3].
The inn’s location is perfect for exploring Cape Cod’s highlights. Nickerson State Park is just a 7-minute drive, Chatham Fish Pier is 9 minutes away, and the Hyannis Transportation Center is a 25-minute trip [2][3]. Whether you’re driving or relying on local transportation, getting around is easy from this central spot.
For guests without a rental car, the inn’s concierge services are incredibly helpful. The staff can arrange transportation and recommend activities within walking or biking distance. As one guest shared:
"Phoebe, is a little more than a personal concierge at your fingertips, she has a boat full of suggestions for sightseeing, excursions, dining, shopping, and more." - Jennifer Y, Tripadvisor Reviewer [9]
If you’re in the mood for some water-based fun, the inn offers kayaks and paddle boards for use right from the property [9]. Guests who meet the minimum stay requirements can also enjoy complimentary harbor tours aboard "A Little Boat" [5]. These perks let you soak in Cape Cod’s natural beauty without venturing far from the inn.
Don’t miss the daily Happy Hours, where you can mingle with fellow travelers and exchange tips about hidden gems and local favorites. Sometimes, the best recommendations come from other guests rather than guidebooks [9].
Throughout this guide, we've highlighted how thoughtful choices - like selecting the perfect room and tapping into local insights - can elevate your Cape Cod getaway. A memorable stay at A Little Inn on Pleasant Bay starts with smart planning and a willingness to embrace its one-of-a-kind charm.
Make the most of the inn's concierge services to uncover local treasures you might otherwise miss. Cape Cod's slower pace is part of its magic, and the inn’s serene ambiance and beautifully styled rooms provide the ideal backdrop for unwinding. Whether you're savoring the European-inspired breakfast with its fresh, homemade offerings or relaxing on one of the inviting porches, this is your chance to step away from the hustle and truly relax.
Take advantage of the exclusive perks offered during your stay. Complimentary bikes let you explore Orleans at your own rhythm, while the homemade treats add a delightful personal touch. The private dock is a gateway to Pleasant Bay's stunning natural beauty, making it easy to enjoy kayaking, paddleboarding, or simply soaking in the views.
Booking early is key to securing your ideal room and travel dates. With just nine uniquely designed accommodations, availability can be limited, so planning ahead ensures a smooth and stress-free experience.
Choosing the right room at A Little Inn on Pleasant Bay comes down to your personal preferences. Many rooms offer picturesque views of Pleasant Bay or the inn's beautifully kept gardens - decide which scenery you’d love to wake up to. Each room has its own character, blending timeless charm with modern amenities, so pick the style and vibe that feels right for you.
To make your stay even more enjoyable, think about practical details like the room size, whether it includes an ensuite bathroom, or if features like air conditioning are important to you. Whether you’re after a snug hideaway or a room with more space to stretch out, the inn has options to suit your needs and ensure a comfortable, memorable visit.
To make the most of your visit to Cape Cod during the bustling summer months, planning ahead is essential. July and August are especially busy, with accommodations booking up fast. Reserving your room well in advance can save you from last-minute stress. Arriving earlier in the day is another smart move - it not only helps you beat the crowds but also makes finding parking much easier.
For a more enjoyable trip, try scheduling your activities during quieter times, like mornings or early evenings. If dining out is on your agenda, making reservations at popular restaurants ahead of time can spare you the hassle of long waits. And don’t forget to venture off the beaten path - exploring lesser-known spots can give you a more laid-back and authentic taste of Cape Cod.
Getting to Cape Cod and exploring the area during your stay at A Little Inn on Pleasant Bay is straightforward, with several convenient travel options available. If you're traveling from Boston, consider taking the Peter Pan Bus Lines, which offers direct routes to various Cape Cod destinations at budget-friendly prices. Prefer flying? Cape Air provides quick flights from Boston to Hyannis, which is just a short drive from the inn.
Once you’ve arrived on the Cape, having a car gives you the most freedom to explore the area at your own pace. However, if driving isn’t your thing, the Cape Cod Regional Transit Authority has you covered. They operate year-round buses and shuttles, with fares starting as low as $2 for a one-way trip or $6 for a day pass. These services make it simple to visit nearby towns and attractions without needing your own vehicle. No matter how you choose to get around, there are plenty of options to ensure your trip is smooth and enjoyable.
If you're looking for a peaceful and personal Cape Cod experience, now's the time to book your stay at A Little Inn on Pleasant Bay. With its quiet setting, friendly hosts, and small seasonal touches that make a big difference, it’s a great place to relax and enjoy the best bed and breakfast in Cape Cod. Whether you’re planning a weekend getaway or a longer break, don’t wait too long—anytime is the best time to visit, and rooms fill up fast.
