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Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond

Photo gallery for Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond

July Hydrangeas
Exterior detail
Property grounds
4 Season Porch
Living room with 50 inch wifi TV with Roku and YouTubeTV

Reviews

10 out of 10
Exceptional
3 bedrooms3+ bathroomsSleeps 6

Popular amenities

  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue
  • Balcony or patio

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1 - King

1 King Bed

Bedroom 2 -Queen

1 Queen Bed

Bedroom 3 - Twin

2 Single 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 rates
Off Season: Sept 30 - May 31: $750 per night 4 night min. $5,250 per week
Spring: June 1 - June 30: $5,978 per week (7 night min)
Summer: July 1 - Aug 31: $6,405 per week (7 night min)
Fall: Sept 1 - Sept 30: $5,978 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.

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About the area

Chatham

Located in Chatham, this holiday home is in the city centre and near the beach. Gallery Antonia and Chatham Railroad Museum are cultural highlights, and some of the area's landmarks include Chatham Windmill and Chatham Lighthouse Beach. Chatham Marconi Maritime Center and Adventure Chatham are also worth visiting. Jet skiing and scuba diving offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby.
View more Holiday homes in ChathamOpens in a new window
Map
Chatham, MA

What's nearby

  • Gallery Antonia - 2 min walk - 0.2 km
  • Chatham Windmill - 10 min walk - 0.8 km
  • Cape Cod Beaches - 16 min walk - 1.4 km
  • Chatham Lighthouse Beach - 19 min walk - 1.6 km
  • Chatham Fish Pier - 19 min walk - 1.6 km

Getting around

  • Hyannis Transportation Center - 28 min drive
  • Hyannis, MA (HYA-Barnstable Municipal) - 47 min drive

Restaurants

  • ‪Cumberland Farms - ‬5 min walk
  • ‪Three Fins Coffee House & Cacao Factory - ‬2 min drive
  • ‪Chatham Bars Inn - ‬12 min walk
  • ‪Chatham Squire - ‬5 min walk
  • ‪Pain D'avignon - ‬13 min walk

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 24 out of 24 reviews
Rating 8 - Good. 0 out of 24 reviews
Rating 6 - Okay. 0 out of 24 reviews
Rating 4 - Poor. 0 out of 24 reviews
Rating 2 - Terrible. 0 out of 24 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Brent B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved the location and the beautiful morning walks to lighthouse beach.
Stayed 5 nights in Oct 2025
Verified

10/10 Excellent

Michael S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Location

We had a great stay at this beautiful Chatham home on a nice private lane off Main Street. Highly recommended!
Stayed 3 nights in Sep 2020
Response from VrboOwner on 11 Sept 2023
We hope you are able to return very soon! Best, Phil and Cheryl
Verified

10/10 Excellent

Jennifer G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Stay

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!
Stayed 14 nights in Jul 2025
Response from VrboOwner on 22 July 2025
You are very welcome and we hope to see you back soon!
Verified

10/10 Excellent

courtney r.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfection in Chatham.

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!
Stayed 7 nights in Jun 2021
Response from VrboOwner on 11 Sept 2023
Hi Courtney, Thank you for the kind review. We look forward to your return next year!
Verified

10/10 Excellent

Breck B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful spot!

Better than advertised and immaculately clean. Great layout, updated kitchen, very well maintained outdoor space. Extremely quiet while still right downtown.
Stayed 7 nights in Aug 2020
Response from VrboOwner on 11 Sept 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!
Verified

10/10 Excellent

Pam C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location

Beautiful house with view of Oyster Pond. Easy walk to center and to baseball field
Stayed 7 nights in Jul 2023
Verified

10/10 Excellent

Robert J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Chatham home

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.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Mike P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay in Chatham!

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.
Stayed 7 nights in Jul 2021
Response from VrboOwner on 11 Sept 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.
Verified

10/10 Excellent

Jay T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location, location, location

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!
Stayed 7 nights in Apr 2021
Response from VrboOwner on 11 Sept 2023
Thanks Jay, we hope you and your family can come back soon!
Verified

10/10 Excellent

Kim S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect beach town getaway

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!
Stayed 57 nights in Oct 2020
Response from VrboOwner on 11 Sept 2023
Thanks for the nice review Kim. We hope you come back and rent again soon!!
Verified

10/10 Excellent

Kathleen H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Location location location.

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.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Ben T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Honeymoon

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!!!
Stayed 7 nights in Sep 2022
Verified

10/10 Excellent

Nancy K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great location

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.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Jeffrey W.

Liked: Cleanliness, communication, location, listing accuracy

Unexpected Gift!

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!.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Philippe G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wish we could have stayed longer

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.
Stayed 7 nights in Jun 2022
Verified

10/10 Excellent

Melissa Gliatta G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay! Loved the house.

Great experience would rent again!
Stayed 3 nights in Sep 2021
Verified

10/10 Excellent

Grace D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gorgeous House in Heart of Chatham

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.
Stayed 5 nights in Sep 2021
Verified

10/10 Excellent

Neil D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chatham charm

Great location close to Oyster Pond and very central to Chatham.
Stayed 7 nights in Aug 2021
Verified

10/10 Excellent

Mark T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great getaway

Beautiful house, perfect location. Will definitely be back.
Stayed 4 nights in Sep 2020
Verified

10/10 Excellent

Julie K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Vacation Home

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!
Stayed 6 nights in Aug 2020
Response from VrboOwner on 11 Sept 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
Verified

10/10 Excellent

Nissa E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Charming House, Prime Location

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.
Stayed 6 nights in Jul 2020
Archival

10/10 Excellent

Caren H.

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!
Archival

10/10 Excellent

Christine L.

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.
Verified

10/10 Excellent

Kyle L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Jul 2025
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