Enjoy the convenience of garage parking - a rare offering in the area.
Discover nearby landmarks
Walk to Cape Cod Beaches
3 bedrooms3+ bathroomsSleeps 6
Popular amenities
Garage parking available
Kitchen
Washer
Air conditioning
Barbecue grill
Balcony or patio
Explore the area
Chatham, MA
Chatham Windmill
Place, Chatham Windmill
10 min walk
Cape Cod Beaches
Place, Cape Cod Beaches
16 min walk
Chatham Fish Pier
Place, Chatham Fish Pier
19 min walk
Hyannis, MA (HYA-Barnstable Municipal)
Airport, Hyannis, MA (HYA-Barnstable Municipal)
37 min drive
Rooms & beds
3 bedrooms (sleeps 6)
Bedroom 1 - King
1 King Bed
Bedroom 2 -Queen
1 Queen Bed
Bedroom 3 - Twin
2 Twin Beds
3 bathrooms, 1 half bathroom
Bathroom 1 -private bathroom off master Bedroom
Toilet · Shower only
Bathroom 2
Bathtub or shower · Toilet
Bathroom 3
Toilet
Outdoor shower
Shower only
Spaces
Deck or patio
Porch or lanai
Kitchen
Outdoor play area
Garden
Dining area
About this property
Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond
A charming 3 bedroom, 2.5 bath cape with large kitchen and private backyard, patio and deck that abuts conservation land. Located on a dead-end, tiny and quiet lane in the center of town just off Main Street in quaint Chatham village.
Walk to shops and restaurants. Oyster Pond beach (0.2 mile / 6 min walk). 1 min walk to Viera on Main bar and restaurant. Chatham Squire a 6 min walk. Lighthouse Beach a 20 min walk, less than a 5 min drive. Chatham A's ballpark an 8 min walk. All beaches with in a 10 min drive.
2026/2027 rates Off Season: Oct 1 - May 31: $854 per night 4 night min. Spring: June 1 - June 30: $6,300 per week (7 night min) Summer: July 1 - Sept 4: $6,510 per week (7 night min) Fall: Sept 4 - Sept 30: $6,300 per week (7 night min)
Cleaning Fee is $250 plus a security deposit is required. A complete linen package, including bed making and stripping is provided. Call to confirm rates and availability. Mass tax is 14.45%.
Security Features To enhance safety and protect the property, there is one outdoor security camera with a sensor spot light mounted above the garage entryway. It is motion-activated for light and camera and records only the exterior approach to the house (driveway) and is marked and can be switched off inside the home if renters prefer.
Also, please view our next door 4 Bedroom cottage. VRBO listing: 108402. 4 night min in off season.
Our prices include all fees. No hidden fees.
Add dates for prices
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
About the neighborhood
Chatham
Located in Chatham, this vacation home is in the city center and near the beach. West Dennis Beach is a popular attraction and the area's natural beauty can be seen at Cape Cod Beaches and Nauset Beach. Chatham Railroad Museum and Chatham Marconi Maritime Center are also worth visiting. Discover the area's water adventures with jet skiing and scuba diving nearby, or enjoy the great outdoors with hiking/biking trails and cycling.
Hyannis, MA (HYA-Barnstable Municipal) - 47 min drive
Restaurants
Cumberland Farms - 5 min walk
Chatham Bars Inn - 12 min walk
Chatham Squire - 5 min walk
Three Fins Coffee House & Cacao Factory - 2 min drive
Dunkin' - 3 min drive
Frequently asked questions
Is Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond?
As of Jul 7, 2026, prices found for a 1-night stay for 2 adults at Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond on Oct 3, 2026 start from $1,035, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking?
Onsite parking is available at the property.
What time is check-in at Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond?
Check-in begins at 3:00 PM.
What time is check-out at Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond?
Check-out is at 10:00 AM.
Where is Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond located?
Located in the heart of Chatham, this vacation home is within a 15-minute walk of Gallery Antonia and Cape Cod Beaches. Mayo House and Chatham Windmill are also within 10 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Our vacation in chatham was just perfect, starting with the beautiful house. Located on a private lane in the center of town, it was the most charming experience!
courtney r.
Stayed 7 nights in Jun 2021
Response from VrboOwner on Sep 11, 2023
Hi Courtney, Thank you for the kind review. We look forward to your return next year!
Thank you Phil for an amazing vacation. The home is wonderful, spotless and very well appointed. You can feel there is pride in ownership. The location is definitely ideal being so close to Main Street yet still felt calm and serene. Overall, it was perfect!
Jennifer G.
Stayed 14 nights in Jul 2025
Response from VrboOwner on Jul 22, 2025
You are very welcome and we hope to see you back soon!
Better than advertised and immaculately clean. Great layout, updated kitchen, very well maintained outdoor space. Extremely quiet while still right downtown.
Breck B.
Stayed 7 nights in Aug 2020
Response from VrboOwner on Sep 11, 2023
Breck and David, thank you for the kind review and I am glad you enjoyed your stay in Chatham. We hope you return next summer!
You would never know that you are only steps away from the bustling Main Street in Chatham. It is a cozy oasis that is perfect for a small family or a gathering of adult friends. One of the very best rentals we have ever enjoyed. Kudos to the owners for providing an upscale but livable property.
This house is kept in immaculate condition. You get all the amenities of a modern house, yet it still has the feel of a seaside cottage. Location is perfect. You are right in the center of town, yet you have complete quiet and privacy since it is located at the end of a dead end just off Main St. The owner is extremely friendly and personable. I would highly recommend staying here.
Mike P.
Stayed 7 nights in Jul 2021
Response from VrboOwner on Sep 11, 2023
Mike, Thanks for the kind words and really glad you had a great stay at the Bearses By Way house in Chatham. Hope to see you back next year.
Loved our stay in Chatham at this beautiful home. And the best feature was its location right behind the shops and on Main St., downtown Chatham. Priceless.
Landlord was super as well. Would totally recommend this!
Jay T.
Stayed 7 nights in Apr 2021
Response from VrboOwner on Sep 11, 2023
Thanks Jay, we hope you and your family can come back soon!
Had an absolutely amazing stay at this beautiful home. It’s conveniently located right in Chatham Center at the end of a small street, so you still have plenty of privacy. The location is perfect for beautiful walks around town, past beaches, and through charming streets. The place had everything you could possibly need for a comfortable stay and was beautifully decorated. Phil was great to rent from, very friendly and helpful. We wanted for nothing while we were there, except for more time! Thank you Phil and Cheryl!
Kim S.
Stayed 57 nights in Oct 2020
Response from VrboOwner on Sep 11, 2023
Thanks for the nice review Kim. We hope you come back and rent again soon!!
Beautiful property in the heart of downtown Chatham. Walk to everything. Dangerous with ice cream so close by. The house was beautifully decorated and spotless. Phil was a pleasure to work with. He answered all our questions and check in was super easy. We hope to return soon. Of our three stays in Chatham this was our favorite property.
The experience renting this property was exceptional. The home is is fabulous and is conventionally located in the town of Chatham yet offers privacy. Walk friendly as well, as the home is located near Main Street. The home exceeded all of our expectations in every way. The owners went out of their way to provide us with a memorable stay in New England during our honeymoon. This property is a must for anyone seeking accommodations in Chatham!!!
We loved the location of this home - right in downtown Chatham. We could easily walk into town for shopping, coffee or dinner. It is nestled at the end of a small alley off Main Street. The house was well stocked, kept very clean and was the perfect rental for our family.
Not being from the area, no one ever knows what to expect when renting a cottage. Well we were amazed. It was more than we could ask for. So well appointed with gorgeous designer fabrics and furniture, and all so tasteful with a nautical feel. Impecably clean and well equipped. The landscape was beautiful and well tended. We created memories that will last a lifetime in this little piece of paradise!.
This house is just about perfect! Right at the quiet end of a dead end alley, this place has parking for two cars, is peaceful, and very clean. The house itself is very well built and well cared for, and finished nicely. The beds are comfortable, the laundry is upstairs, and you can walk to main st in about 60 seconds.
The owner is easy to communicate with, and everything was easy.
Easily the nicest house I have ever rented.
Perfect location for a girls’ trip at the end of summer. The house was bigger and more beautiful than the pictures let on. Quintessential Cape decor, comfortable bedrooms, clean, well equipped kitchen, cozy decks, patio and sunroom for relaxation, conversation or a cocktail—all within easy walking distance to Chatham Lighthouse Beach, Main Street shopping and some of the best restaurants on the Cape. Just park your car and no need to drive anywhere. We enjoyed our stay tremendously and hope to visit again.
This home was not only a beautiful home, it was clean and located within walking distance to many shops and restaurants and only minutes away from many beaches. Perfect!
Julie K.
Stayed 6 nights in Aug 2020
Response from VrboOwner on Sep 11, 2023
Julie, We are so glad you enjoyed your stay at our home in Chatham. We hope you plan to come back next summer or sooner!
Best, Phil and Cheryl
This home is clean, charming, and well equipped. It felt like we were in a modern countryside cottage, secluded with neighbors only on one side. Yet a 1 minute walk would put us in the middle of Main Street. Three porches allowed us to enjoy the outside without leaving the property. We would definitely rent this place again.
Nissa E.
Stayed 6 nights in Jul 2020
Archival
10/10 Excellent
Caren H.
Aug 31, 2016
Chatham Summer
Staying in your home made our vacation superb! The location was perfect for all the activities that our family loves, including walking to town to restaurants, movies, Chatham A's baseball games, Friday night band concerts & sunsets at Oyster Pond. It was the perfect setting for a fabulous summer. Your home is so clean, comfortable and spacious. We can't wait to come back!! Thanks Phil & Cheryl for providing excellent customer service and for sharing your home with us!
Caren H.
Archival
10/10 Excellent
Christine L.
Sep 21, 2015
Beautiful home & perfect location
This is our second year staying at 39 Bearses. We love the location, it is right in the heart of Chatham and walkable to everything the town has to offer. You can even walk to Oyster Pond which is a great beach for kids. The house itself is in perfect condition, clean and well maintained with everything you need while away from home. Everything is new and well kept inside and outside, the kitchen and bathrooms are beautiful and nicely laid out for families. The owners are very quick to respond and answer any questions you might have. Even though you are right in downtown Chatham, Bearses By Way is a nice quiet street. We are looking forward to coming back again next year.