Entire home

Chatham Landmark Estate, Large Guest House, Pool 177-CF

Photo gallery for Chatham Landmark Estate, Large Guest House, Pool 177-CF

Aerial view of the estate that looks over Eastward Ho! golf course.
Large heated pool with cabana & changing rooms.
Welcome to "The Port"!
Main house kitchen fully equipped with modern appliances.
Cozy seating area.
Reviews
10 out of 10 Exceptional
8 bedrooms7+ bathroomsSleeps 18409 sq m

Popular amenities

  • PoolPoolPool
  • Pet-friendlyPet-friendlyPet-friendly
  • WasherWasherWasher
  • DryerDryerDryer
  • Air conditioningAir conditioningAir conditioning
  • KitchenKitchenKitchen

Explore the area

Map
Chatham, MA
  • Popular LocationFox Hill4 min drive
  • Popular LocationChatham Fish Pier5 min drive
  • Popular LocationChatham Lighthouse7 min drive
  • AirportHyannis, MA (HYA-Barnstable Municipal)27 min drive

Rooms & beds

8 bedrooms (sleeps 18)

Guest Bedroom #1

2 Queen Beds

Guest Bedroom #2

2 Single Beds

Guest Bedroom #3

1 Queen Bed

Guest Bedroom #4

2 Single Beds

Guest Bedroom #5

2 Single Beds

Guest Bedroom #6

2 Single Beds

Primary Bedroom #1

1 King Bed

Primary Bedroom #2

1 King Bed

7 bathrooms, 1 half bathroom

Ensuite for Guest Bedroom #3

Toilet · Shower only

Ensuite for Guest Bedroom #4

Bathtub or shower · Toilet

Guest House

Bathtub or shower · Toilet

Guest House

Bathtub or shower · Toilet

Main House

Toilet · Shower only

Powder Room

Toilet

Primary Bathroom #1

Toilet · Shower only

Primary Bathroom #2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Garden
Dining Area

About this property

Chatham Landmark Estate, Large Guest House, Pool 177-CF

This property is professionally managed by Pretty Picky Properties

Chatham Landmark Estate, Awesome Barn/Guest House, Pool

Sleeps 18
8 Bedrooms, 7.5 Bathrooms
Rents Friday to Friday during peak season
Linens included, beds made
Pool is open from Memorial Day through Columbus Day weekend.
Pets Considered

As you roll up the extended driveway and catch your first glimpse of the homes, you realize the impressive individuality of this property. From the Federalist style side gambrel roof on the expanded Colonial main house to the thoroughly exposed wood posts, beams and rafters inside, this place retains the unique charm demanded by its original sea captain owner 220 years ago.

First, soak in the location and setting. Here you have 1.61 acres of artfully landscaped privacy, abutting the upscale Eastward Ho! private golf course, with beautiful Pleasant Bay beyond. The carefully kept, expansive lawns make a wonderful and safe play space for children. Note the line of grape arbors leading to an unexpected wishing well.

Your private, heated pool is a large one, complete with its own freestanding and well equipped cabana. When you need some beach time, it's only a two-minute drive over to Jackknife Cove Beach on Pleasant Bay.

Or go in the opposite direction for a minute more and discover Strong Island Landing Beach.

Inside the two story main manor house, centuries' old charm mingles perfectly with thoughtful renovation for the best of beauty, function and comfort. The completely updated and outfitted kitchen adjoins a handy breakfast nook and flows into one of the most impressive dining rooms you'll ever experience.

There are three separate lounge and gathering places on the main level, a living room, sitting room and family room. Two of the main house's six bedrooms and 2.5 of its baths are located here as well.

The upper level provides another four bedrooms, including two primary suite bedrooms with ensuite baths and two other bedrooms, one with two queens and one with two twins - (Note: Can be converted to a king-size bed with ample notice). There is also another full bath upstairs.

Enter the nearby Guest House/Barn, and it's hard not to gape at the expanse and sheer visual impact of the great room, so aptly named. It's positively gigantic in every way, accentuated by the soaring ceiling with its dramatic exposed beams and rafters.

The rest of the Guest House includes a second fully equipped kitchen, two more bedrooms and two more full baths. Please note that the barn will not have the water on Mid-October through April for off-season stays.

The 4,350 square feet of the Main House and Guest House combined are centrally air conditioned or serviced by high efficiency split units. There is also high speed Wi-Fi, as well as several smart flat screen TVs with cable. NOTE: the main part of the barn is not air conditioned, just the bedrooms and the kitchen/living room area.

Please enter your travel dates for up-to-date pricing. This property has a seven-night minimum during the peak season. As is customary in vacation rentals there are additional fees to the rates listed. Those fees include a reservation fee and a non-refundable Accidental Damage Protection (ADP) fee totaling $225. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 14.45%.

This property offers a three-night minimum stay during select weeks in May–June and September–November. Guests are charged a cleaning fee for all stays less than seven nights. Stay seven nights or more and the cleaning fee is waived.

Be sure to search this site for more Pretty Picky Properties - your best selection of prime vacation homes available for summer rental on Cape Cod.

Property manager

Pretty Picky Properties

Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Air conditioning

House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

Important information

You need to know

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

About the area

Chatham

Located in Chatham, this holiday home is near the beach. West Dennis Beach is a popular attraction and the area's natural beauty can be seen at Cape Cod Beaches and Cape Cod National Seashore. Adventure Chatham and Cape Cod Lavender Farm are also worth visiting. Discover the area's water adventures with kayaking, surfing/body boarding and fishing nearby, or enjoy the great outdoors with cycling.
Map
Chatham, MA

What's nearby

  • Fox Hill - 4 min drive
  • Chatham Fish Pier - 5 min drive
  • Chatham Lighthouse - 7 min drive
  • Harwich Port - 11 min drive
  • Ocean Edge Golf Club - 17 min drive

Getting around

  • Hyannis Transportation Center - 27 min drive
  • Hyannis, MA (HYA-Barnstable Municipal) - 27 min drive

Restaurants

  • Chatham Pier Fish Market - 5 min drive
  • Mac's Chatham Fish & Lobster - 6 min drive
  • Chatham Perk - 4 min drive
  • Corner Store- Chatham - 5 min drive
  • Dunkin' - 6 min drive

Frequently asked questions

Is Chatham Landmark Estate, Large Guest House, Pool 177-CF pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at Chatham Landmark Estate, Large Guest House, Pool 177-CF?

Check-in begins at 4:00 PM.

What time is check-out at Chatham Landmark Estate, Large Guest House, Pool 177-CF?

Checkout is at 10:00 AM.

Where is Chatham Landmark Estate, Large Guest House, Pool 177-CF located?

Situated by the sea, this holiday home is within a 10-minute walk of Cape Cod Beaches and Caleb Nickerson House. Fox Hill and Chatham Shark Center 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.
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Rating 10 - Excellent. 10 out of 10 reviews" "
Rating 8 - Good. 0 out of 10 reviews" "
Rating 6 - Okay. 0 out of 10 reviews" "
Rating 4 - Poor. 0 out of 10 reviews" "
Rating 2 - Terrible. 0 out of 10 reviews" "

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Steven S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great House for Family
The Cape Cod Home is large, with plenty of space for our 12 guests to dine together, lounge comfortably, with plenty of separate for small groups to hang out. Managers were quite responsive to our questions.
Stayed 5 nights in Dec 2023

10/10 Excellent

Meaghan W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Reunion Weekend
The house was beautiful and accommodated our group well. pretty Picky properties was very helpful and responsive to any questions about the property. We had a great weekend!
Stayed 3 nights in Sep 2023

10/10 Excellent

Anthony D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Experience in Chatham
I was with a large group for a golf trip and we had an amazing stay at this property. The house was clean, check in/out was easy, and they provided an online guest book which was great to reference with any questions I had. The house is great for outdoor activities and located close to many golf courses and restaurants. Would highly reccommend!
Stayed 3 nights in Jun 2023

10/10 Excellent

Conrad E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Cape Cod Idylic Property
An amazing 1800s Cape Cod house, modernised and fantastic 1.6 acres with lovely pool and tree house for kids as well as immaculate gardening and landscaping.
Stayed 6 nights in May 2023

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
This house was PERFECT for our large group
This house was absolutely perfect for a large group out on the cape for a golf trip. The house is in great condition, ton of space both inside and out, bedrooms were comfortable and good sized as well. We also utilized the bedrooms in the barn, which are just as comfortable as the rooms in the house. Also felt very private w/ a golf course bordering the property. It really was the perfect house, hope to be back
Stayed 3 nights in Sep 2022

About the host

Hosted by Pretty Picky Properties

Host profile image
There are a lot of places to rent for a summer vacation on the Lower Cape. There are only a few Pretty Picky Properties. Most are directly on or very near the beach. Our homeowners love their properties, fastidiously maintain them, and expect guests to treat them accordingly. Our guests demand a prime location and a vacation experience that far exceeds the typical Cape summer rental.

When you spend a good amount of money for a perfect summer vacation, you want to be sure before you commit. That's why we take the time to carefully and completely answer all your questions by phone or email. If you can visit the Cape in advance, we'll be happy to show you one or more properties you're considering.

Most guests are also comforted to know that Pretty Picky also has a property management division. Most unforeseen property issues can be resolved quickly with our ready access to maintenance resources.

We look forward to helping you plan your ideal Cape Cod vacation!

The Pretty Picky Team
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