Facing the ocean, this vacation home features 8 bedrooms and 6 bathrooms, accommodating 18 guests. It offers a balcony, patio, and yard for outdoor enjoyment, along with nearby golf. Explore water sports at the marina and visit the Atwood House Museum and Chatham Windmill.
Highlights
Room to spread out
Enjoy spacious layout that give everyone more room to relax.
Beach equipment
A rare find — beach equipment ready to go for your days by the sea.
Centrally-located
You're never far from where you need to be with this convenient location.
8 bedrooms6+ bathroomsSleeps 18
Popular amenities
Private pool
Balcony or patio
Toys
Barbecue grill
Washing machine
Air-conditioning
Explore the area
Chatham, MA
Atwood House Museum
Place, Atwood House Museum
3 min drive
Mayo House
Place, Mayo House
5 min drive
Chatham Lighthouse Beach
Place, Chatham Lighthouse Beach
6 min drive
Hyannis, MA (HYA-Barnstable Municipal)
Airport, Hyannis, MA (HYA-Barnstable Municipal)
41 min drive
Rooms & beds
8 bedrooms (sleeps 18)
Bedroom 1
2 Single Beds
Bedroom 2
1 King Bed
Bedroom 3
1 King Bed
Bedroom 4
1 Queen Bed and 1 Double Sofa Bed
Bedroom 5
2 Single Beds
Bedroom 6
2 Single Beds
Bedroom 7
1 Queen Bed
Bedroom 8
1 King Bed
6 bathrooms, 1 half bathroom
Bathroom 1
Towels provided · Bathtub or shower · Bathtub · Toilet
Bathroom 2
Towels provided · Toilet · Shower only
Bathroom 3
Towels provided · Bathtub or shower · Toilet
Bathroom 4
Towels provided · Toilet · Shower only
Carriage House Bathroom
Towels provided · Toilet · Shower only · Hair dryer
Outdoor Shower
Outdoor shower
Powder Room
Towels provided · Toilet
Spaces
Deck or patio
Porch or lanai
Outdoor shower
Kitchen
Balcony
Separate dining area
Garden
Dining area
About this property
Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.
New heated gunite pool. 18X40 with automatic pool cover, and completely fenced in for safety. Design includes many plantings and grass to complete this idyllic garden. The space also includes an outdoor shower, and rinsing station, plus multiple patios and seating areas for hours of outdoor sun and entertaining.
Perfect for large groups, families traveling together, family reunions, or anyone looking for a little more space! Bring your extended family, au pair, or a vacation with multiple families at this expansive 6,000 sq ft home that sits privately on a fenced 1-acre yard.
Have your morning coffee atop the widow’s walk with 180-degree views of Nantucket Sound, Monomoy Island, Stage Harbor Lighthouse, and the Atlantic Ocean. Relax or sunbathe on the roof deck. Eat, visit, and entertain on the screened-in porch. Go back to the widow’s walk to see the sunset. There are so many choices to take in the sea air and sunshine on this property.
This large estate is perfectly situated to comfortably sleep 16+ while maintaining space and privacy. The bedrooms are clustered in pairings of 2, with a shared bathroom. These sleeping quarters are completely separate from one another. The first floor has one BR with an en-suite bathroom and an additional 2 BR that share a bath. Upstairs includes 2 private quarters, each with 2 BRs and 1 bathroom.
The Caboose is the epicenter of this home. It is a historic, vast open space with high ceilings and beautiful natural light. It has 3 couches, a fireplace, and multiple tables set up for games, checkers, and cards.
The Living Room is a cozy alternate space for sitting and watching the 55-inch TV. The Dining Room has a long mahogany table that sits 12 comfortably. The kitchen is fully equipped, with top-line appliances, 2 sinks, and an island to sit at for morning coffee, afternoon tea, and nighttime cocktails.
In addition, there is a separate carriage house, featuring a king bed, living room, galley kitchen, and bathroom. The carriage house is equipped with another 55-inch TV, a perfect place for the kids' movie night while the parents enjoy an adult dinner in the main house. This estate has so much to offer!
The Sears Point neighborhood is teeming with other families and children, and the quiet lanes and cul-de-sacs make it a perfect place to safely walk, and ride bikes. Let the kids run and play in the grassy, expansive 1-acre yard. The property is completely fenced-in.
This property offers privacy and space, with easy proximity to all Chatham has to offer. Take a 10-minute bike ride to the center of Chatham - or a 1.3-mile walk/run to the center of town. Take a two-minute stroll and drop your kayaks & paddle boards into Stage Harbor from the landings on Sears Point. Drive 5 minutes to Oyster Pond - easy parking, clean bathrooms, and shallow water make this Chatham’s best beach for young families. If you desire the bigger beaches, it is only a 5-10 minute drive to Lighthouse Beach, Ridgevale Beach, or Hardings Beach.
Please note that we do not allow wedding receptions or any events on the property out of respect for our fellow neighbors and community. Sunday to Sunday rental. 1-week minimum peak season.
No pets, no exceptions.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
Chatham
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
No pool use after 10 pm out of respect for neighbors
No use of fireplaces
Important information
You need to know
Property Registration Number C0115480550
Property # 789503vb
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Chatham
Located in Chatham, this holiday home is near a water park and near the beach. Atwood House Museum and Chatham Railroad Museum are cultural highlights, and some of the area's landmarks include Chatham Windmill and Mayo House. Travelling with kids? Consider Chatham Marconi Maritime Center and Adventure Chatham. Kayaking, waterskiing and water tubing offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
Hyannis, MA (HYA-Barnstable Municipal) - 33 min drive
Restaurants
Cumberland Farms - 5 min drive
Chatham Bars Inn - 6 min drive
Chatham Squire - 5 min drive
Three Fins Coffee House & Cacao Factory - 6 min drive
Snowy Owl Coffee Espresso Bar - 6 min drive
Frequently asked questions
Does Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.
have a pool?
Yes, this property has a pool. Pool types include heated pools.
How much does it cost to stay at Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.
?
As of 21 Sept, 2026, prices found for a 1-night stay for 2 adults at Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.
on 1 Dec, 2026 start from S$31,843, 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.
Is Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.
pet-friendly?
No, pets are not allowed at this property.
How much is parking at Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.
?
On-site parking is available at the property.
What time is check-in at Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.
?
Check-in begins at 4:00 PM.
What time is check-out at Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.
?
Checkout is at 11:00 AM.
Where is Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.
located?
This family-friendly Chatham holiday home is located by the sea, within 2 mi (3 km) of Atwood House Museum, Chatham Railroad Museum and Mayo House. Chatham Windmill and Chatham Lighthouse are also within 3 miles (5 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
28 Harbor Hill Road was an outstanding choice for our 3 generation family beach vacation. The house is well maintained, with plenty of room for our 3 families to spread out. The pool is really nice and the kids spent tons of time swimming. The grill is new and works great. The owners stocked the garage with plenty of beach chairs, umbrellas, and beach/pool toys. Downtown Chatham is a quick car ride or 20 minute walk. The owners were super-responsive whenever we had a question.
Our hosts were very responsive and helpful. They have a beautiful property, conveniently located for all our needs. The widow's walk deck provided a terrific view of sunsets and backdrops for family photos. We all had a wonderful time and would definitely book this property again.
We couldn’t have better things to say about our stay!! This served as our families home base for my wedding weekend. Dan was so hospitable and the house/property was everything we could have wanted and more. The house is large and spacious- great for a big group. The pool was heated and the backyard beautiful! We now have wonderful memories here!
Wonderful stay at this classic New England coastal house with an absolutely perfect property. We made so many memories in the stately great room, on the patio grilling out, and of course, in the amazing pool! Everyone, especially our kids, had the absolute best time and we look forward to staying again.
This home was perfect for our family reunion. There were multiple comfortable areas for hanging out. The host was very responsive, and the place is stocked with toys and games. We would definitely rent it again.
Check in very easy. House worked perfectly for us, our adult kids, snd grandkids. Beach in morning and pool in afternoon were divine! The house has lots of room to spread out. Hope to come back! We all loved it!
Showers were unsafe with no hold bars to hold on to prevent falls in slippery tubsI. No hand railing on any entrance to house. No hand railings to assist in safely entering pool. Basically the house was unsafe for seniors . These safety upgrades wouldn’t be very expensive and should have been provided for a house in this price range..We could not use the pool because there was no way to safely enter pool. Bob Metcalfe
Stay was great. Big house for the 15 of us, pool, large dining room table, Carriage House was a plus! We had excellent communication with the owner who was incredibly responsive!
We were a group of 13. Ages 3-67. Worked for everyone. The yard, pool, ping pong,location. All were perfect. Can’t thank the owners enough.
Stayed 14 nights in Jun 2025
Verified review
10/10 Excellent
Sara D.
31 Aug, 2018
Wonderful house for large families!
The house is beautiful, meticulously maintained and perfect for large groups. We comfortably fit 8 adults and 5 children. Proximity to town is so convenient, we enjoyed morning walks to get coffee each day. Oyster Pond is also a quick walk or drive and a perfect beach for families with small children. The owners are welcoming and set you up for a great trip - we tried almost all of their recommendations. We loved our time in Chatham!
We had a wonderful stay and this home was perfect for our parent’s 50th wedding anniversary celebration! There was plenty of space for everyone to spread out (6 families) with multiple bedrooms and comfortable common areas. The large family room easily accommodated all of us, and the adorable courtyard provided easy access to the back bedrooms. We especially loved the second-floor porch and the screened-in porch, which was perfect for relaxing any time of day.The pool was amazing and a huge hit with everyone. It was stocked with tons of pool toys, and the large, beautifully manicured yard gave the kids plenty of room to run and play. The homeowners have clearly put a lot of thought into making guests feel at home. Everything was well labeled, making it easy to find what we needed, and the kitchen was stocked with every utensil imaginable. We did not use the BBQ but it looked new. We also appreciated all of the thoughtful extras, including beach towels, plenty of beach chairs, shampoo and conditioner dispensers in the bathrooms, and two washers and dryers, which made traveling with a large group so much easier.The widow's walk was a really neat feature with beautiful views, although it's definitely something to keep in mind if you're afraid of heights or have small children.The location was great—close to several beaches and everything we wanted to do. We truly had a lovely time and would absolutely stay here again!
This is a beautiful Cape Cod home in a beautiful neighborhood. The rooms in the home are separated in such a way that it was great for our family of 11 so that each family had almost their own small wing. GG and Grandad stayed in the Carriage house apartment which provided peace and quiet. The pool was fantastic and used every day, you could walk to town in 20 minutes or to a beach in about 8 minutes. The host was extremely helpful in guidance about the property and things to do in the area since we were visiting from California and did not know the area. We will stay there again.
First off, communication with Dan was stellar from booking through the stay itself. He is highly responsive and honest and took care of the few small issues we had.
Secondly, the photos and descriptions of this house don't do justice to how expansive and roomy it is. There are several different "wings" that give your family/group a real sense of space. The common areas (especially the screened porch and great room) are fantastic for indoor relaxing, and the pool was wonderful, easy to use, and warm!
Incredibly serene neighborhood 5 minutes from Chatham, an easy walk to Lighthouse Beach, gorgeous sights and sounds of the Cape in all directions!
The property and location were perfect for our family. The house had everything we needed and more. It was clean and the beds were comfortable. We are a large family and there were no complaints. Everyone enjoyed the beautiful home and pool!
The house location was perfect for us. I was a little concerned that we were in a crowded neighborhood, I should not have worried. The home is in a neighborhood, but you cannot see your neighbors at all. The first day we saw three wild turkeys!
We walked and biked to downtown Chatham. The beach was a short drive. We ordered fresh seafood dinners from the fishing pier and it was delicious! I would recommend this home for your next vacation in Chatham.
Our extended family (14: 9 adults, 5 children) had a nice stay in Chatham.Positives: Excellent pool and pool area; teens loved the independent apartment above the garage; responsive host; beautifully kept yard.Negatives: Inconsistent temperature regulation around the house, particularly in one upstairs area (hosts put in room A/Cs to help but they were loud and modestly effective); upstairs bathroom required people to crouch that were 5'9"; main room not furnished for a large group comfortable gathering; one upstairs area did not have warm water.Our family has rented several places like this over the years at around this price point (22k/week; 3k/day). At that rate, we expect that all sleeping and living areas to be quite comfortable, but that was variable in this case. Overall, we had a very nice stay, and it would deserve an excellent rating with pricing more consistent with the quality of the rooms as a whole.
Our family of 15, including 8 adults, 3 teenagers and 4 children between 4 and 11 stayed here for a week. It was a perfect rental. The 8 bedrooms accommodated us perfectly, as the children were able to stay in proximity to their parents in two separate areas on the second floor. The Carriage House bedroom worked for the parents ORT eh teenagers who stayed on the first floor of the main house with us, the grandparents. The house is incredibly well-maintained, and the large swimming pool was delightful.The kitchen is as well equipped with appliances, utensils and cookware as any restaurant, and even with our large group, we never ran out of cutlery, plates, or glassware. The many public rooms on the first floor provided locations for individual groups who wanted to read, do puzzles, play games, cook, or eat. The house is located on a very quiet street about 1.5 miles from the center of town, and a little over a mile from a small cove beach. The owners have stocked the garage with all of the beach chairs, coolers, sand toys and beach umbrellas that one could ever need. A beach/trail walk starts very near the house.
This residence could not have been more perfect. Thank you!
We recently had the pleasure of staying at this Chatham Estate with a group of 14, ranging in age from 10 to 81. This property exceeded all our expectations and provided a perfect setting for our multi-generational family reunion.
Property Highlights:
• Heated Pool: The new heated gunite pool was a highlight for everyone. It was large enough for our group to enjoy together. The automatic pool cover and fenced-in design provided safety and peace of mind for the younger members of our family. The surrounding garden with plantings and grass created a beautiful and serene environment.
• Outdoor Spaces: The multiple patios and seating areas offered plenty of options for outdoor relaxation and entertaining. The outdoor shower and rinsing station were convenient after a day at the beach.
• Carriage House: The separate carriage house was a fantastic addition, providing a king bed, living room, galley kitchen, and bathroom. Was great for those without kids.
Conclusion:
Chatham Estate is an exceptional property that offers privacy, space, and a variety of amenities for large groups and families. The combination of a beautiful heated pool, spacious interiors, and an ideal location made our stay unforgettable. Highly recommended for anyone looking for a luxurious and accommodating getaway.
Absolutely beautiful home, great location, excellent amenities & fully stocked for anything you could need or want. The owners were very responsive & helpful throughout the booking process & our entire stay. Our extended family of 16 people from 77 years old down to 4 years old had a perfect week! Thank you for sharing your beautiful home!
Beautiful property and home. Great for family gatherings with heated pool, main house and carriage house. Very quiet screened porch wonderful for morning coffee or tea, or evening drinks, games etc. we had one maintenance problem with the refrigerator and the owner was very attentive in getting it addressed. When we weren’t sight seeing cape cod we were either in the great room, screened porch or pool. Very relaxing.
We had a wonderful time due in no small amount to the house and our wonderful hosts. The house is impressive. Plenty of room for the 7 adults and 5 kids we had (one bedroom was never used). Lots of dishes, pots and pans, washers and dryers, refrigerators made moving in a breeze. Dan provided a very complete set of instructions and information about beaches and restaurants. Any questions I had were promptly answered. The pool was a wonderful addition to our visit. Though it didn't keep us from visiting our favorite beaches, it was used daily. We will have great memories of our 50th anniversary get together. Thank you Dan and Kim.
The home is lovely and spacious. The various wings and groupings of bedrooms are ideal for multiple families, allowing for privacy.
The kitchen is well outfitted for cooking and serving big meals. The neighborhood and surrounding area can't be beat. The new pool, an added plus.
Our multi-generational family is hoping to return, again. My communication with the owner was stellar. Thank you for sharing your Chatham home with us!
Love our stay in Chatham! House was the perfect size for our family. 17 people ages 6 months to 68 years! Bedroom layout allowed everyone to have their own space at night. Location was central to lots of activities and we always loved returning to the house after a day of exploring the cape. And the pool was the icing on the cake! Thanks!!
Stayed 7 nights in Jul 2021
About the host
Hosted by Kimberly Capello
We live in Concord, Massachusetts. We have 3 girls who love sea creatures and the beach! Dan is from Harrisburg, PA, and I am from Deerfield MA. I grew up vacationing with my family on Cape Cod for a couple weeks every summer. We both attended Georgetown University. Go Hoyas! When Dan and I met, I introduced him to Chatham (in fact he got roped into helping my parents do work on their cottage!).
Why they chose this property
We have been vacationing in Chatham for 20 years. We finally had the opportunity to purchase this special property in 2015. This home is what we call a "rambler". It appears very unassuming from the front, but when you enter, you find that the house just keeps going! We fell in love with it the first time we saw it. It offers wonderful space, and privacy for multiple families. It has multiple options for outside living and entertaining. We would like to share this special place and the amazing town of Chatham with others!
What makes this property unique
The Caboose was added to the home in 1970. It was the original waiting room of the Harwichport Rail Station. This room is massive! It has the original fireplace, with original chipped fish tiles. When the light comes through the original leaded glass windows it is just amazing! With three sofas and a game table, this space is perfect for cocktails, reading, resting, and playing board games and cards. The nautical rope railing, the amazing views from the widow's walk, the full sun-exposed roof deck.... these are just a few of the things that we love about this home. We have worked very hard updating the home, while still maintaining it's character. If you are looking for a home with amazing charm, blending the old and new, this is the place for you!