Chatham Estate. Heated Pool, Sleeps 16+, AC, walk to beach! 1.3 mi from town.

Chatham, Massachusetts
$3604 avg/night
Minimum Stay 7 Nights
Bed 8

Bed

Bath 5

Bath

Home Private Vacation Home

Property Type

Sleep 18

Max Sleeps

Night 7 nights

Min Stay

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.



Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Beach Sun Loungers Beach Towels Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    8 Bedrooms Bed Sheets Provided
  • GENERAL

    Double-glazed Windows Recycling Unit Size: 6000 Sq Ft (557 Sq M) Uses Some LED Lighting
  • KITCHEN

    Dishwasher Ice Maker Lobster/crab Pot Microwave Oven Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Car Recommended Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Fenced Yard Garden Outdoor Furniture
  • POOL/SPA

    Fence Around The Pool Heated Pool Private Pool
  • BATHROOMS

    5.5 Bathrooms Bathtub Or Shower Hair Dryer Outdoor Shower Shared Bathroom Toilet Paper Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Basketball Nearby Birdwatching Nearby Cycling Nearby Fishing Nearby Fitness Facilities Nearby Golf Nearby Golfing On Site Kayak On Site Sailing Nearby Swimming Nearby Water Tubing Nearby Windsurfing Nearby
  • ENTERTAINMENT

    Arcade/game Room Books Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Dinnerware Children's Games Children's Toys Highchair Travel Crib
  • LOCATION HIGHLIGHTS

    In A Village Near A Health Or Beauty Spa Near A Hospital Near The Sea
  • SERVICES AND CONVENIENCES

    Housekeeping (on Request) Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 18

Map Map

School District Availability

Review Review

  • Bob M.

    Submitted Jun 15, 2026

    Stayed Jun 8, 2026

    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

  • Meghan M.

    Submitted Jun 5, 2026

    Stayed May 27, 2026

    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!

  • Paul S.

    Submitted May 28, 2026

    Stayed May 21, 2026

    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.

  • William B.

    Submitted Sep 18, 2025

    Stayed Sep 2, 2025

    Large historic house with a great yard.

  • David S.

    Submitted Aug 28, 2025

    Stayed Aug 17, 2025

    Great family vacation spot! Plenty of room for large family to spread out.Hosts very easy to communicate with. Would absolutely return.

  • Susan L.

    Submitted Aug 17, 2025

    Stayed Aug 10, 2025

    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!

  • Brian N.

    Submitted Jul 21, 2025

    Stayed Jul 13, 2025

    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.

  • Nancy O.

    Submitted Jun 29, 2025

    Stayed Jun 15, 2025

    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.

  • Kate B.

    Submitted Sep 22, 2024

    Stayed Aug 18, 2024

    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.

  • Jeff M.

    Submitted Aug 18, 2024

    Stayed Aug 11, 2024

    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.

Your dates are Available!

Total

Includes taxes and fees
$3,604+
View details