• Sleeps: 24
  • Bedrooms: 10
  • Bathrooms: 9
  • Pets: 0
(14 reviews )
"Second Wind" -- An Orleans estate with large heated pool, on Town Cove

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Peak Summer Weeks starting at $25,400, plus tax
Sleeps up to 24 in three dwellings
Linens and bed making included
Pets Considered up to 25 lbs.
Weddings not permitted on property

Guest house renovations for 2020! Master bedroom with new ensuite bath with fantastic views!


Please click on the "Virtual Tour "tab to take a 3D tour of the home

Please note:  This property rents Sunday to Sunday in summer for full-week or multiple week terms only, but is available during the shoulder-season for weekends and special events.  Click HERE for a spectacular Aerial Tour

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 new pool and spa at the main house. There’s plenty of room for everyone to gather around the fire pit and cook out poolside in 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 Main House has 5 bedrooms, 2 full baths and 3 half baths. The Carriage House is steps away with 2 more bedrooms and 2 full baths with a full kitchen. The carriage house went through a major renovation in 2018 to include a master suite on the first floor and expanded and remodeled full bath upstairs. The third structure, the Guest House, is located down by the water with gorgeous views of Town Cove from every room. The Guest House is outfitted with 3 bedrooms, 2 full baths, fully equipped kitchen and a hot-tub.

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 an in ground pool (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 and explore the in-land waterways of Nauset Cove and Nauset Marsh. Bring your boat and use the adjacent boat ramp to motor your way to Nauset Beach by boat!

Inside the Main House, you have an updated kitchen with granite counters and new appliances. 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 movies.
Upstairs in the Main House, there are 3 bedrooms: 1 master suite with a King bed and a private full bath, 1 room with a Queen, and one room with a set of bunks (full size bed on the bottom). A second full bath is also upstairs with a tub/shower combination. There is a Queen bedroom on the main floor with a private half bath. On the lower level, you'll find an extra sleeping area with 2 twin beds for overflow sleeping. A half bath is also located on the lower level with an outdoor shower not far away.  
Next door in the carriage house, you'll find a second full kitchen, a living area, Master 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 bedroom with a Queen and 2 twins.
The Guest House was fully remodeled in the fall 2015 – 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. The other bedroom upstairs features a king size bed and stunning views of Town Cove. The second full bath is located upstairs. 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 the 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 $125 reservation fee and an $80 non-refundable Accidental Damage Protection (ADP) fee and a refundable security deposit of $2,000. 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.

  • Air Conditioning (Central)
  • Beach Chairs
  • Beach Towels
  • Blender
  • Boat Friendly
  • Books
  • Cable TV
  • Ceiling Fans
  • Classic Cape Decor
  • Coffee Maker
  • Covered Porch
  • Deck
  • Dishwasher
  • Fully Equipped Kitchen
  • Grill (Gas)
  • Grocery Provisioning (for a fee)
  • Hair Dryer
  • Hot Tub
  • Ice Maker
  • Kayak(s) for guest use
  • Kids Toys
  • Linens Included (beds made)
  • Lobster Pot
  • Microwave
  • Near Bike Trails
  • Non-Smoking Home
  • Outdoor eating area
  • Outdoor Fire Pit
  • Outdoor Play Space
  • Outdoor Shower (enclosed)
  • Pets Considered
  • Ping Pong Table
  • Portable Fans
  • Private Chef Available
  • Private Lot
  • Private Pool
  • Rents Sunday to Sunday during peak weeks
  • Resort/Reunion Property
  • Smart TV/Apple TV
  • Sonos System
  • Stand Up Paddle Board(s) Provided
  • Stereo
  • Toaster/Toaster Oven
  • Updated Interior
  • Updated Kitchen
  • Walk to Salt Water
  • Walk to Town/Village
  • Washer/Dryer
  • Waterfront
  • Water View
  • Wine Bottle Opener
  • Wireless Internet (WiFi)
  • Checkin Available
  • Checkout Available
  • Not Available

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Room Bedroom Details Baths TVs Comments
Master Bedroom
  • Private Full Bath
  • King Bed
  • Step-in Shower
  • Full Bath
TV Main House Upper Level
Bedroom 2 Queen Bed
    TV Main House Upper Level
    Bedroom 3
    • Bunk Beds
    • Full Bed
        Main House UpperLevel
        Bedroom 4
        • Private Half Bath
        • Queen Bed
        Half Bath TV Main House Main Level
        Bedroom 5
        • Private Full Bath
        • Twin Bed (2)
        • Step-in Shower
        • Full Bath
          Main House Lower Level
          Bedroom 6
          • Private Full Bath
          • King Bed
            TV Carriage House Main Level Master Bedroom
            Bedroom 7
            • Queen Bed
            • Twin Bed (2)
                Carriage House Upper Level
                Bedroom 8
                • Private Full Bath
                • Queen Bed
                • Step-in Shower
                • Full Bath
                TV Guest House Main Level
                Bedroom 9
                • Bunk Beds
                • Twin Bed (1)
                • Trundle Bed
                  TV Guest House Upper Level
                  Bedroom 10
                  • Private Full Bath
                  • King Bed
                    TV Guest House Upper Level Master Bedroom

                    including taxes and fees
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