Captain Isaiah House: 033-Y Classic Sea Captain's House, Walk/Bike to Everything

Top rated by guests
Welcome to Yarmouth
Walk into a beautiful new kitchen
Open concept Kitchen
Plenty of room to cook
Back patio area with outdoor shower
review stars
10Outstanding
(11 Ratings)
"We had a wonderful stay at the Captain Isaiah house! Everything was clean and the property was beautiful. Having a digital copy of all the instructions and amenities was super helpful for our group. W..."
Meaghan C.
Don't miss out! Price and availability may change
10 / 10
Outstanding(11 Ratings)

House in West Dennis, MA

16 guests · 7 bedrooms · 4 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this house rental

This home is professionally managed by Pretty Picky Properties.

Classic Sea Captain's House, Former Bed & Breakfast, Walk/Bike to Everything

Sleeps 16
8 Bedrooms, 4.5 Baths
Rents Saturday to Saturday in Peak Summer
Linens Included, Beds Made
Pets Considered

If you've never been in this tony Bass River neighborhood, you're in for a pleasant surprise. Many of the extraordinary homes here, including this one, were custom built by Quakers in the mid-19th century. This property's charming original features have been preserved, while ongoing renovations are increasingly adding today's creature comforts.

Location: At this property, you're a couple of homes back from Bass River with a peek at the water. You can bike to small but sandy Windmill Beach in about four minutes, or ride another four or five minutes to the much larger Smugglers Beach. The ride is half the fun, as your route runs right along the picturesque river.

You can also bring your boat and launch it at the town landing, very close to this property.

The Cultural Center of Cape Cod is your next-door neighbor, where you'll discover galleries, concerts, hands-on classes, and creative opportunities of all kinds. Hungry for breakfast? Walk five minutes to the heart of Bass River Village and the Crazy Rooster Pub and Grill. Try the cranberry pancakes. Then check out the Bass River Mercantile, a classic general store where time stands still. You'll be moved to buy some one-of-a-kind gifts and very special mementos of your Cape Cod vacation.

There are several other tempting restaurants within easy walking distance of the property as well.

Outdoor Living Spaces: The outdoor spaces at this property are likely what make it so appealing for large groups on summer vacations. It begins with the covered front porch featuring classic wooden rocking chairs. Nearby, there's a sizable screened porch off the kitchen, equipped with a small café table and chairs, along with plenty of extra seating. At the back, an umbrella-shaded dining table sits on the deck, which leads down to a stone patio with a wood-burning fire pit—perfect for stargazing after dark. The area also includes a gas grill and an enclosed outdoor shower. The large, flat grassy yard is ideal for kids to run and play safely. Don't forget to visit the side of the garage where kayaks and SUPs are stored on racks—help yourself! The owner even provides a cart for transporting them, and a neighborhood boat landing is just a two-minute walk away. Viewing the house from the street reveals the all-new white clapboard siding, updated windows, and well-maintained landscaping, matching the pristine appearance of other homes in this neighborhood.

Kitchen and Dining: You'll be pleased with this large, fully renovated and fully equipped kitchen. All top-of-the-line, stainless-steel appliances here, including a giant gas range with six burners and two ovens, plus two dishwashers. You'll have your choice of a Keurig or a standard drip coffee maker. The attractive granite counters include a large center island with three highboy chairs for counter seating. Walk from the kitchen to the dining room with its extra-large wooden dining table and seating for up to eight. But you'll no doubt choose to dine on the private outdoor deck.

Living Spaces: Continue through the dining room to the generous living room, which extends 32 feet, the entire width of the house. In addition to the lounge seating, there's a glass-topped table and wicker chairs, a perfect place to tackle the obligatory family vacation puzzle. The main level provides one full and one-half bath. There's also a small office just off the entrance foyer for anyone who needs to work remotely while in residence.

Sleeping Arrangements: There is one bedroom on the main level. It's a good-sized room with a comfy queen-sized bed. On the second level, accessible from either of two stairways, you'll find five more bedrooms and three full baths. The primary bedroom has a TV, a gas fireplace, and its own full private en-suite bath. Two other bedrooms each have a queen bed. Another has two twin beds, and the final bedroom on this level has a bunk bed with a full bed under a twin. The laundry is also located on the second level. There's a second washer and dryer in the basement.

Walk up a narrow stairway to the third level of this house, and you'll discover two more sleeping spaces, one with a full-size double and a twin, the other with two twins. There is no bathroom on this level, and given the low ceilings and unconventional stair access, this third level is most suitable for children of sufficient age, who will likely appreciate having the space to themselves.

Please enter your travel dates in the top right corner of this page for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Damage Protection fee totaling $255.00 In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%.

Please be sure to search this site for your best choice of prime vacation homes available for summer rental on Cape Cod.

It's your vacation. Get Picky! ®

Amenities at Captain Isaiah House: 033-Y Classic Sea Captain's House, Walk/Bike to Everything

Non-smoking
Pets allowed
Family friendly

Map of West Dennis, MA


Ratings and reviews

10 / 10
Outstanding(11 Ratings)
10 / 10Outstanding·May 2026
We had a wonderful stay at the Captain Isaiah house! Everything was clean and the property was beautiful. Having a digital copy of all the instructions and amenities was super helpful for our group. We will definitely be recommending this property to friends and family!
10 / 10Outstanding·Jul 2025
Wonderful house and location! We were incredibly happy with our stay and as a family of foodies we really appreciated the well appointed kitchen!
10 / 10Outstanding·Jul 2025
This house was just perfect for our family's annual vacation. With 8 bedrooms, all 16 of our family members had just what they needed (no young children in the group). Many enjoyed the used of the kayaks and paddle boards on the Bass River, just a short walk away. One feature of the house we specially liked were the 2 side-by-side dishwashers in the kitchen. One was always going as the other was being filled. The house and yard were well maintained, and we enjoyed several evenings around the fire pit in the back yard.
10 / 10Outstanding·Jun 2025
There were 16 of us and the property was perfect for our group. Plenty of space to gather together or to spread out. We also fit 10 cars in the driveway. Loved it!

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Captain Isaiah House: 033-Y Classic Sea Captain's House, Walk/Bike to Everything. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Captain Isaiah House: 033-Y Classic Sea Captain's House, Walk/Bike to Everything pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Captain Isaiah House: 033-Y Classic Sea Captain's House, Walk/Bike to Everything?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.