$2,218 - $5,415 per night

Second Wind 039-O

House hosted by Pretty Picky Properties

  • 24 guests
  • |
  • 10 bedrooms
  • |
  • 10.5 baths
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Book direct and save up to$921per night.

About The Property

"Second Wind" - An Orleans Estate with large heated pool, on Town CoveSleeps up to 24 in three dwellings Linens and bed making included Pets Considered up to 25 lbs. Weddings not permitted on property Pool is open Memorial Day - Columbus Day To view a slide show with captions, click on icon in upper right corner of the photo. Please click on the "Virtual Tour "tab to take a 3D tour of the home Or click here to see a video presentation of the property Please note: This property rents Friday to Friday in summer for full-week or multiple week terms only, but is available during the shoulder-season for 3-night stays.  This Orleans Estate is located in the heart of Orleans Village on picturesque Town Cove. Bring the whole family and leave the cars in the driveway for the week. You'll spend countless hours around the pool and spa at the Main House. There’s plenty of room for everyone to gather around the fire pit and cook out poolside at the outdoor kitchen. You can walk to everything in Orleans Center, including some of the best restaurants in town, village shops and of course, ice cream. There are four ice cream shops within walking distance! The mid-century homes have been recently updated with all the modern conveniences while retaining much of the original charm. The large 1.3 acre lot is waterfront on Town Cove and has a heated pool and spa (open Memorial Day - Columbus Day). The large lot provides plenty of recreation space on the gently sloping lawn. Hold your own version of the Whiffle Ball World Series. Town Cove is a great place to drop an owner-provided kayak or SUP and explore the in-land waterways of Nauset Cove and Nauset Marsh. Bring your boat and use the adjacent town boat ramp to motor your way to Nauset Beach by boat! The Main House underwent a full remodel in 2023, you have an updated kitchen with granite counters and new appliances, including a huge side-by-side refrigerator and two dishwashers. There are two dining areas along the back of the house so that large groups can dine together. There is also an enclosed porch overlooking the lawn, pool and cove beyond. The house is great for bringing family together but you have enough space to spread out as well. There are 3 large seating areas in the Main and Carriage Houses that are great spots to watch a ball game or for the kids to watch their shows/movies. The Main House has 5 bedrooms, 5 full baths and 1 half bath. You'll find one of two primary suites on the main level of the Main House with a king size bed, sitting area and beautiful ensuite bath. There is also a powder room on the main level and living room with separate card-table room. Upstairs in the Main House, there are 3 bedrooms: the second primary suite with a king bed and a private full bath, the second bedroom features a king size bed and ensuite bath, and the third bedroom has a queen size bed with a twin bunk above. There is a full bath for guests of this room in the hallway with a tub/shower combination. In the lower level, you'll find an extra sleeping area with 2 twin beds for overflow sleeping. Plus a wonderful new media room, laundry room and there is a full bath down here as well plus an outdoor shower not far away.   Next door in the Carriage House, you'll find a second full kitchen, a dining area, a powder room, a primary suite with king size bed and a private full bath on the main level. Upstairs in the Carriage House, you'll encounter a loft space with a TV and cozy couch. There is a second full bath and a bedroom with a queen sized bed plus 2 twins.The third structure, the Guest House has been fully remodeled – brand new kitchen with stainless steel appliances and granite counters. On the main level is a queen bedroom with full bath while upstairs you have a kid’s room with a bunk bed (full under a twin) and another twin with trundle bed with an en suite bath. The primary suite upstairs features a king size bed and stunning views of Town Cove with a wonderful en suite bath. The shower feels like an outdoor shower! In addition, the Guest House has an outdoor shower and 6-person hot tub overlooking the Cove. All three homes have AC, WIFI and cable TV.If you feel like leaving your own private resort, good news – two world famous beaches are less than 5 minutes’ drive away, Nauset Beach on the Atlantic or Skaket Beach on Cape Cod Bay. There is nothing that is overlooked at this ideal vacation property for larger groups. 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 $ 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 the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It's your vacation. Get Picky! 


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Pretty Picky Properties

Brewster, Massachusetts224 Properties

Jim and Karen started Pretty Picky Properties as a result of meeting a need they had themselves. After deciding to rent their prized cottage in Brewster, they became frustrated with the lackluster marketing and absence of on-site attention their property received from their conventional rental broker. So they did it themselves. They tapped Jim’s 35+ years of marketing and advertising experience and applied Karen’s personal relationship management skills, honed in 30+ years as an educator. The

Orleans, Massachusetts 02653

Location provided after the reservation is made.

Safety & Inspections

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