Pleasant Bay Remote Work/Play Getaway - OSMITH
Orleans Rentals

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  • Type: Single Home
  • Bedrooms: 4
  • Max. Occupancy: 10
  • Baths: 3 full 1 half
  • Town: Orleans
  • Neighborhood: Orleans - South Orleans
  • Proximity to Water: Waterfront to .1 Mile

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NEW FALL AND WINTER RATES: 1 Week at $4500, 2 Weeks for $8000, 3 Weeks for $9500, and a 32-day Month for $12,000 (14.45% tax is not applied to short-term rental over 31 days).

The owners refer to this one-of-a-kind property as Pleasant Plus. This unique beachfront home and certified wildlife habitat is located on Big Pleasant Bay with spectacular panoramic water and big sky views from the Atlantic Nauset barrier beach to the golf course at Chatham's Eastward Ho! Country Club.

Set on a bluff, the main house is an amazing, white-washed, full Post and Beam design. The first floor offers a family-friendly open floor plan with oversized fully equipped kitchen, dining area and living room with vaulted ceiling and open loft. There is one half bathroom in the foyer and one full bathroom with tub/shower at the end of a center hall, as well as two guest bedrooms; one with a queen bed and one with two twin beds.

Step out of the family room onto a full-length deck looking south onto the fall/winter kaleidoscope of down-Cape weather, certified natural wildlife habitat, and relentless local and migratory bird activity.

On the second floor you will find a stunning master bedroom with king-sized bed where you will wake each day overlooking the breathtaking vista. This floor also features a separate full bathroom with shower, a third guest bedroom with one double bed and two small twin beds, and a fully tech-equipped "work from vacation" office setting and/or kid-friendly entertainment area for reading, creating, gaming or just relaxing.

The lower walkout-to-beach level features a large glass-walled indoor bathroom to accommodate guest and beach-goers alike, as well as an all-weather (above freezing) outdoor shower with view of Strong Island.

Stairs descend south from the Bay side of the house to the 1100 square foot boathouse/party house built directly on the private sandy beach where guests can isolate and commune with the Bay's nature and beauty up close and personal at any time, and in any weather.

Pleasant+'s isolation from public activity (down a 1/3 mile private lane, into a gated cul-de-sac) make the property an ideal cathartic getaway from the realities of urban living. Unique features of this all-season home make it possible to experience the wonders of Lower Cape Cod's fall and winter natural and wildlife beauty, all the while remaining engaged and connected as remote work-from-home responsibilities may require.

Amenities include: Panoramic view of Pleasant Bay from all living areas, central heating and air conditioning, high-speed wired and WiFi internet service, full home office/WFH setting, first floor washer and dryer, 3 smart TVs with live streaming service, DVD/VHS player, telephone, light duty laser printer, gas grill, Keurig and drip coffee makers, enclosed outdoor shower, seasonal outdoor furniture, kayak, dinghy, beach chairs and recliners, sporting and aquatic gear, etc. Linens are provided upon request.

Additional Fees: $125 Non-Refundable Reservation Fee, $300 Cleaning Fee, $1000 Refundable Security Deposit, plus State and Local Taxes apply. If linens are provided by owner, a $150 fee would apply for unlaundered linens left by tenants taken from security deposit.


++INCLUDED WITH YOUR STAY IS A FREE ACTIVITY PACKAGE: (1 each of the following per day up to 28 vacation days): Round of Golf, Round of Mini Golf, Ferry Ride to Martha's Vineyard or Nantucket, Whale Watch, Bicycle Rental, and the P-town Monument. Specific Activity Locations Provided. Activities subject to change and availability per season.

Bed Sizes

  • Bedroom 1 - King
  • Bedroom 2 - 2 Twins
  • Bedroom 3 - Queen
  • Bedroom 4 - 1 Double (Full) & 2 Twins


  • Bathroom 1 - 1st FL; Half Bath
  • Bathroom 2 - 1st FL; Full - Tub/Shower
  • Bathroom 4 - Lower Level; Full - Shower
  • Full Baths - 3.00
  • Half Baths - 1
  • Bathroom 3 - 2nd FL; Full - Shower
  • Beach - Private Beach
  • Beachfront
  • Maximum Parking - 6
  • No Pets
  • Smoking Not Allowed
  • Telephone
  • Vacuum
  • View - Waterview Ocean
  • Iron & Board
  • Hair Dryer
  • Blender
  • Coffee Pot - Keurig & Drip
  • Crock Pot
  • Dishwasher
  • Lobster Pot
  • Microwave
  • Toaster
Indoor Amenities
  • Extra Room - Loft
  • Fireplace
  • King Bed
  • Washer & Dryer
  • Air Conditioning - Central
  • Ceiling Fans
  • Fans - One Portable Fan
  • Heat
  • CD Player
  • DVD Player
  • Internet Access - WiFi
  • Stereo/Radio
  • TV - 3+ TVs
  • TV Service - Streaming Only
Outdoor Amenities
  • Outdoor Furniture
  • Picnic Table
  • Grill - Gas Grill
  • Patio Umbrella
  • Outdoor Shower - Enclosed
  • Deck
  • Stairway to Beach
  • Beach Chairs


First Night Last Night Daily Rate Weekly Rate Monthly Rate
10/24/20 10/30/20 N/A $4,570 N/A
10/31/20 11/06/20 N/A $4,570 N/A
11/07/20 11/13/20 N/A $4,570 N/A
11/14/20 11/20/20 N/A $4,570 N/A
11/21/20 11/27/20 N/A $6,270 N/A
11/28/20 12/04/20 N/A $4,570 N/A
12/05/20 12/11/20 N/A $4,570 N/A
12/12/20 12/18/20 N/A $4,570 N/A
12/19/20 12/25/20 N/A $6,270 N/A
12/26/20 01/01/21 N/A $6,270 N/A
01/02/21 01/08/21 N/A $4,570 N/A
01/09/21 01/15/21 N/A $4,570 N/A
01/16/21 01/22/21 N/A $4,570 N/A
01/23/21 01/29/21 N/A $4,570 N/A
01/30/21 02/05/21 N/A $4,570 N/A
02/06/21 02/12/21 N/A $4,570 N/A
02/13/21 02/19/21 N/A $4,570 N/A
02/20/21 02/26/21 N/A $4,570 N/A
02/27/21 03/05/21 N/A $4,570 N/A
03/06/21 03/12/21 N/A $4,570 N/A
03/13/21 03/19/21 N/A $4,570 N/A
03/20/21 03/26/21 N/A $4,570 N/A
03/27/21 04/02/21 N/A $4,570 N/A
04/03/21 04/09/21 N/A $4,570 N/A
04/10/21 04/16/21 N/A $4,570 N/A
04/17/21 04/23/21 N/A $4,570 N/A
04/24/21 04/30/21 N/A $4,570 N/A


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Specific to This Unit:

Fall & Winter Specials

1 Week at $4500 (dropped from $6000/week)

2-Weeks for $8000 (save $1000)

3-Weeks for $9500 (save $4000)

32-day month for $12,000 (with tax savings) - save $7734 in rate and tax savings 

Valid from 01/01/2019 to 03/31/2021

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