House in Chatham, MA
18 guests · 8 bedrooms · 5 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
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About this house rental
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.
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.
Amenities at Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.
Non-smoking
No pets allowed
Map of Chatham, MA
Ratings and reviews
10 / 10Outstanding·Jul 2026
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!
10 / 10Outstanding·Jul 2026
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!
10 / 10Outstanding·Jun 2026
This is a comfortable, well-appointed, rambling home with lots of group play and hangout space.
5 / 10·Jul 2019
We were stunned by how beautiful the property was when we first drove up. But then when we stepped inside, we were even more delighted to find well-decorated rooms, a great layout for multiple families staying together (different areas of the house allow for privacy while sharing large well-appointed common areas), tons of fun board games and whiffle ball, a kitchen with new fully functioning high-end appliances that was stocked with all the essentials and more, and excellent air conditioning. We were four families, totaling 16 people, ranging from 3-80 years old, and we all had a wonderful time. The kids and some adults enjoyed long hours of playing whiffle ball, the teens and adults relaxed on the porches and widow's walk, some of us enjoyed being able to run / walk to Chatham lighthouse, and we all enjoyed long family dinners at both the house and in Chatham. The check-in and check-out process was a breeze. The owners were great about providing insight for our planning of our week there and checked in with us after we arrived to make sure everything was perfect. All in all it was a perfect rental for a large family reunion, and we would rent it again if we are in Cape Cod!
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Top rated by guests
10Outstanding
(52 Ratings)
"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 co..."
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