Sail Loft: 489-C Updated Chatham Family Compound, Heated Pool w/Hot Tub, Walk to Town/Beach

Chatham, Massachusetts
$2175 avg/night
Minimum Stay 3 Nights
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 3 nights

Min Stay

This property is professionally managed by Pretty Picky Properties

Updated Chatham Family Compound, Heated Pool with Hot Tub, Walk to Town/Beach

Rents Friday to Friday in Peak Season
Linens Included, Beds Made
Pets Under 25 Pounds Considered

Pool is open from Memorial Day to Columbus Day weekend

If you relish the charm of Chatham but love modern amenities, here's the resort style vacation destination for your group. The acre-plus property provides two separate structures with sleeping for up to 10. The in-ground heated pool is the focus of summer outdoor living here, further embellished by the hot tub.

The property's location is ideal. You can walk or bike to the restaurants, shops and entertainment unique to Chatham Village. Or slip into your swimsuit, grab a towel and head to nearby Oyster Pond Beach or famous Lighthouse Beach, your choice. Each less than a 15-minute walk.

The larger main house features a big covered outdoor patio with a dining table, plenty of seating and a gas grill. The patio overlooks the pool house and pool less than 100 feet away. The pool house adjoins the surprisingly large pool, surrounded by a roomy stone deck with a dining table, plenty of lounge and other seating, an outdoor shower, gas grill and beverage center, fire table and, of course, the tempting spa.

Inside the main house, you'll be delighted by the fully outfitted, renovated kitchen with granite counters and a center island with built-in gas range top. The kitchen walks out to the patio for convenient serving when you dine outside. You'll also find a handy half bath just off the kitchen. There's a good sized dining room with a patio view. The large, comfortable living room adjoins the dining room and offers a flat screen TV.

The main level also has a small den/office with a another TV seating area for the kids to watch shows/movies. The home has high speed Wi-Fi, a SONOS system, and is centrally air conditioned. The primary bedroom suite is also on the main level and includes a big king size bed and a remodeled full bath en suite. There is also a flat screen TV.

On the upper level of the main house, there are two bedrooms, one with a king size bed. The other bedroom has four twins. These two bedrooms share a roomy full bath.

The pool house offers rustic, lodge-like charm with exposed beams and vaulted ceiling in the full kitchen and adjoining family room/TV lounge. The kitchen is fully equipped and includes a round dining table and chairs. The pool house has a main level bunk room with four twins. There is also a ping pong table on the main level and a full bath. The upstairs sleeping area has a small lounge area with another TV and a step-up section with a comfortable king size bed.

That upper level walks out to a second level deck overlooking a natural vista of undeveloped woodlands.

Please enter your travel dates in the top right corner of this page 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 $255.00. 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 3-night minimum stay during select weeks in May – June & September – November. Guests are charged a cleaning fee for all stays less than 7-nights. Stay 7-nights or more and the cleaning fee is waived.

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

It's your vacation. Get Picky! ®

Town of Chatham Registration #286

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly Service Animals Exempt From Fees
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

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

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2500 Sq Ft (232 Sq M)
  • KITCHEN

    Cookware/dishes/utensils Dishwasher Ice Maker Microwave Oven Refrigerator Spices Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill
  • POOL/SPA

    Heated Pool Hot Tub Private Pool
  • BATHROOMS

    3 Bathrooms Bathtub Or Shower Hair Dryer Outdoor Shower Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Cycling Nearby Golf Nearby Swimming Nearby Whale Watching Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Arcade/game Room Games Stereo Table Tennis Smart TV With Cable/satellite Service
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    In A Village Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Availability

Review Review

  • Caroline K.

    Submitted Jun 8, 2026

    Stayed Jun 4, 2026

    Perfect house for a big group!!

  • bonnie s.

    Submitted Jun 3, 2026

    Stayed May 28, 2026

    House and pool house both terrific. Property grounds very well maintained, many bunnies running about. Table on the outside porch at main house was perfect for Bingo and appetizers, held all of us with room to spare.Location close to beaches,and town. Atwood Museum was wonderful, only 1 from our group went, she really enjoyed it. Rainy day b'day party was held in the pool house which by the way sleeps 6. Only issues we had, jetts didn't work in the hot tub, hooks needed by the front door, pool guy who was so nice showed up late and everyone out of the pool for 45 mins. Lawn guys came late Fri. aft., zoomed about and did a nice job. Difficult to see leaving the property, hedges should be trimmed, might be next door neighbor. Comfortable, roomy main house and beds and pillows comfy. Had a great time.

  • Lynn C.

    Submitted May 29, 2025

    Stayed May 23, 2025

    We had a great stay at the sail loft! Beautiful property in a great location with all the amenities! Would love to return!

  • Brendan B.

    Submitted Oct 28, 2024

    Stayed Oct 11, 2024

    Was a great property. Plenty of space for our group of 8. Main house had everything we needed, with a great layout, good common areas, good kitchen, and a great outdoor space w/grill. Pool house was great as well - plenty of space w/a full kitchen - great for families with kids. Town and beach were walkable - great location.

  • Dillan K.

    Submitted Oct 10, 2024

    Stayed Oct 4, 2024

    We had a group of friends staying at the Chatham bars inn for a wedding and thought we’d explore other options in the area. While everybody enjoyed their stay in the Cape, we had a lot of envious friends and family that wished they had stayed with us at this beautiful property. We will definitely be back.

  • Mitch A.

    Submitted Jul 4, 2024

    Stayed Jun 27, 2024

    We absolutely loved this property. Amazing location, beautiful gardens and a very comfy and welcoming home. Wonderful all around.

  • Kasumi K.

    Submitted Aug 28, 2023

    Stayed Aug 18, 2023

    We had a wonderful weeklong August family vacation at this property. The check-in process was very smooth and easy with a very nice personal greeting from a property manager. The house was ready to welcome us and have fun. The garden was beautiful and lawn was large enough for children and adults to enjoy with multiple activities. The house had plenty of outdoor and indoor games for us to enjoy as well. The pool was very clean and had plenty of seating and umbrellas. The hot tub was a huge hit with the adults and we enjoyed star gazing every night. Communications with the property manager was very easy as they were just a text away and they responded very quickly. It was a vacation we will remember fondly always thanks in huge part to how seamless the stay was. Thank you!

  • Steven C.

    Submitted Sep 11, 2022

    Stayed Sep 5, 2022

    Quintessential Cape Cod property. Beautiful grounds and beautiful. The Sail Loft is wonderful if you need some privacy or multiple families. Walk to town or lighthouse

  • Kristi K.

    Submitted Jul 26, 2022

    Stayed Jul 16, 2022

    We had an amazing week! All 12 of us slept comfortably and thoroughly enjoyed the space. The pool and yard space were a huge plus for the kids!

  • Susie M.

    Submitted Jul 5, 2022

    Stayed Jun 25, 2022

    The house was great! It was nice to have 2 separate buildings, each with a kitchen. There was enough space for us to be together or spread out. We really enjoyed the pool too!

Your dates are Available!

Total

Includes taxes and fees
$2,175+
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