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

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your current months are February, 2025 and March, 2025.
February 2025
March 2025

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

Flat-screen TV, books, stereo
Beach nearby
Fridge, microwave, oven, stovetop
Exterior
Golf

Reviews

10 out of 10
Exceptional

Entire home

8 bedrooms8 bathroomsSleeps 18409 sq m

Popular amenities

  • Parking available
  • Pet-friendly
  • Washer
  • Pool
  • Barbecue grill
  • Air conditioning

Explore the area

Map
Chatham, MA
  • Caleb Nickerson House
    ‪9 min walk‬
  • Chatham Shark Center
    ‪4 min drive‬
  • Fox Hill
    ‪4 min drive‬
  • Hyannis, MA (HYA-Barnstable Municipal)
    ‪27 min drive‬

Room options

Similar properties

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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 king size bed - (Note: Can be converted to two twin-size beds 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 not that the Guest House (Barn) is fully winterized from Mid-October through April for off-season stays each year. As a result the property only has 6 bedrooms and 5.5 bathrooms sleeping a maximum of 14 guests. **

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.
During your stay at this holiday home, you're just a quick walk from Cape Cod Beaches. Enjoy your stay with amenities like a private pool and a kitchen in the holiday home.
  • Air-conditioned home with private pool, kitchen and washing machine
  • Within a 10-minute walk of Cape Cod Beaches and Caleb Nickerson House
Chatham Landmark Estate, Large Guest House, Pool 177-CF offers its guests barbecue grills and a garden. The front desk is open around the clock.

Property manager

Pretty Picky Properties

Languages

English

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Heated pool
  • Private pool

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Chef service

Bedrooms

  • 8 bedrooms
  • Bedsheets provided

Bathroom

  • 7.5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Living room

Entertainment

  • Books
  • Flat-screen TV with cable/satellite channels
  • Games
  • Stereo

Outdoor areas

  • Barbecue grill
  • Garden
  • Patio

Laundry

  • Laundromat nearby
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoke-free property

Location highlights

  • Near a hospital
  • Near the sea

Things to do

  • Golf
  • Heated pool
  • Birdwatching nearby
  • Cycling nearby
  • Fishing nearby
  • Golfing nearby
  • Kayaking nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Whale watching nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden
  • Unit size: 4,400 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Pets

  • Pets are welcome
  • Service animals are exempt from fees.

Children and extra beds

  • Children are welcome.

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.
Property Registration Number C0292260550

Property is also known as

466621
Vrbo Property
Chatham Landmark Estate, Large Guest House, Pool 177-C Chatham

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

Reviews

10

Exceptional

Rating 10 - Excellent. 13 out of 13 reviews" "
Rating 8 - Good. 0 out of 13 reviews" "
Rating 6 - Okay. 0 out of 13 reviews" "
Rating 4 - Poor. 0 out of 13 reviews" "
Rating 2 - Terrible. 0 out of 13 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

Pamela H.

Liked: Cleanliness
Wonderful stay at The Port
Our family of 14 gathered for an event over the weekend. The Port is a gorgeous property that easily accommodated our group. The home was well appointed, with comfortable bedrooms and numerous sitting areas where we could gather separately or together. We highly recommend The Port!
Stayed 3 nights in Nov 2024

10/10 Excellent

Shaun D.

Liked: Cleanliness
Beautiful Home
Perfect place for a family vacation and plenty of outdoor space for activities. Large eating tables and spaces to enjoy meals together.
Stayed 3 nights in Sep 2024

10/10 Excellent

Rebecca A., Briarcliff Manor

Liked: Cleanliness
Fab Family Retreat
Spectacular home and property. Rain or shine we had a terrific trip!
Stayed 8 nights in Jul 2024

10/10 Excellent

Steven S.

Liked: Cleanliness
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
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
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
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
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

10/10 Excellent

Donald V.

Liked: Cleanliness
Great place
Nice location great house would rent agaib
Stayed 7 nights in Aug 2022

10/10 Excellent

Lorraine G.

Liked: Cleanliness
Beyond expectations
We all enjoyed our stay. The house and “barn” was amazing. I was happy that everyone from ages 8 to 74 had a great time with all the amenities. Location was perfect
Stayed 7 nights in Jul 2022

10/10 Excellent

Abbye S.

Liked: Cleanliness
Private Oasis In Chatham
From the moment you drive up until the minute you leave the property, this beautifully landscaped private oasis is truly a vacation destination. The beautiful main house has everything that you could ask for with lots of room and areas for entertainment. The carriage house can accommodate more people if you need it with a two extra bedrooms and bathroom upstairs, a kitchen, den, and bathroom downstairs, a huge open game room, but most of all, a huge outdoor dining area for those great summer nights. The heated pool is very large and fun to play or swim laps in. I cannot say enough of how great the entire place is and the people who manage it. It was a very relaxing, hassle free, summer vacation.
Stayed 7 nights in Jul 2022

10/10 Excellent

Valerie B.

Liked: Cleanliness
Elegant, spacious, unique Cape property
Unique combination of elegant, private spaces for everyone to sleep; many areas for gathering in the main house, in the "barn", and outside; two well-equipped kitchens; a lovely pool; and beautiful grounds.
Stayed 7 nights in Jul 2022

10/10 Excellent

Gerald R.

Liked: Cleanliness
Family Gathering
Property was fabulous and the management company made things easy. Great place!!!
Stayed 7 nights in Jul 2022