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Massachusetts | Cape Cod

Second Wind Estate

10 bedrooms·10.5 bathrooms·24 guests·5900 sq/ft

Views of the water

In the heart of Orleans Village, perched on the scenic shores of Town Cove, lies a majestic Orleans Estate designed for family, fun, and making memories. It's a place where leaving your car in the driveway feels natural, as all the allure of Orleans Center is but a short stroll away. Indulge in sumptuous meals at renowned restaurants, discover delightful village shops, and, for those sweet cravings, choose from four inviting ice cream parlors nearby. This waterfront haven boasts three distinct structures, each dripping with mid-century charisma yet rejuvenated with contemporary flair. The Main House, having recently undergone a comprehensive 2023 remodel, delights with its modern kitchen, dual dining areas, and a tranquil enclosed porch offering panoramic views of the verdant lawn, pristine pool, and serene cove. Both the Main and Carriage Houses feature ample seating areas, perfect for family gatherings or a cozy movie night. The Carriage House itself is a marvel, with a full kitchen, luxurious suites, and an enchanting loft space. But it's the Guest House, with its captivating Town Cove views from every room, modern kitchen, and a hot tub poised for stargazing, that might just steal your heart. Every detail here has been thoughtfully curated to inspire relaxation and recreation. Whether it's taking a dip in the heated in-ground pool, embarking on a kayaking adventure using the owner-provided equipment, or challenging loved ones to a Whiffle Ball match on the sprawling lawn, the opportunities for joy are endless. From the primary suites with king-size beds and spa-like en suite baths to the playful kids' rooms with snug bunk beds, there's a corner for everyone. With state-of-the-art amenities like AC, WIFI, and cable TV standards across all homes, comfort is a given. This is not just a vacation rental—it's the backdrop to unforgettable family stories waiting to be written.

Our promise

We've reviewed thousands of homes and approve only the best. Each one is professionally managed and vetted for comfort and style, raising the bar for every stay.

Amenities

Indoor

Air conditioning

Dryer

Internet

Washer

Outdoor

Outdoor grill

Heated pool

Hot tub/Jacuzzi

Pool

Cornhole boards

Misc

Beach chairs

Beach towels

Board games

SONOS system

Portable fans

Elevate your stay with add-on services

Book a home, then customize your experience. From beach gear delivery to pre-arrival groceries and private chefs, we coordinate everything you need so you can make memories in the waves and stories at sunset.

Private chef

In-home massage

Beach rentals

Pre-arrival groceries

Alcohol delivery

Private driver

Bedroom details

Bedroom 1: King

Bedroom 2: King

Bedroom 3: Queen + Twin

Bedroom 4: King

Bedroom 5: Two Twins

Bedroom 6: King

Bedroom 7: Queen + Two Twins

Bedroom 8: Queen

Bedroom 9: Single Over Double Bunk + Twin + Trundle

Bedroom 10: King

Location

Inside the destination

Neighborhood: Orleans Center - Located in the heart of Orleans Village on picturesque Town Cove. - Proximity 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.

Parking information

Parking spaces are available.

Reviews

Kate

We absolutely enjoyed our stay! Property Management team was so responsive to any question and the house was in impeccable shape. Our family stayed during the pandemic and the house was spotless. we had 19 people (9 of which were kids)and everyone really enjoyed themselves. pool is exceptional, rooms spotless and comfortable, and the location of the house made it easy to walk to beach, market, and restaurants. we had one issue with the fire pit and the property management team responded to our issue within seconds! we had an amazing experience and hope to stay again in the future

Policies

Check-in: 4:00 PM

Check-out: 10:00 AM

Quiet Hours: 8:00 PM - 8:00 AM

No smoking allowed

No events allowed

Pets welcome

Cancellation policy

Plans change, we get it.

Enjoy peace of mind when booking with KEY.co.

75% Refund: Receive a 75% refund when you cancel your reservation at least 120 days before check-in.

No Refund: Reservations canceled 119 days or less before check-in are not eligible for a refund.

Refunds subject to a 25% processing fee of the total.

Things you need to know

A private Chef is available.

Pool is open Memorial Day - Columbus Day

All bed linens and bath towels are provided at the premises.

Utilities to the property during the rental term will be provided. Such utilities include electricity, cold and hot water, natural gas (if applicable), heat, and trash removal.

Provided with a starter set of cleaning/paper products. There will be paper towels and bath tissue to start off your week. Similarly, you will be provided with cleaning products like dish soap, laundry detergent, all-purpose cleaners, etc. We ask that you replace what you use so the guests coming in after you can enjoy the same convenience. Some kitchen trash bags will also be provided.

Restrictions

The minimum night of stay varies by time of the year.
No more than the listed number of persons, including infants, children and overnight visitors listed on the lease shall occupy said premises and shall not permit more than the listed number of vehicles on the lease to be parked in the spaces assigned to the premises at any time. No camper vehicles that provide sleeping accommodations of any kind will be allowed without prior approval.
No smoking, animals, birds, or pets of any description shall be allowed on the leased premises (unless otherwise noted on the lease). Violation of any of these policies will result in a $5,000 penalty charged to the account on file.
The tenant is responsible for and agrees to notify the Landlord's Agent before departure of all damage, loss, and/or added expense to the premises during the lease term, including pay-per-view TV charges, except normal wear and unavoidable casualty which may result from occupancy. Failure to notify the Landlord's Agent before departure of all known damages or losses may not result in the application of the Accidental Damage Protection Program.
The tenant shall allow the Landlord or Landlord's Agent to enter the premises upon reasonable request and notice, both inside and outside, to inspect the premises, to make repairs thereto, and/or to protect the premises.
Use of illegal materials such as fireworks at the property is prohibited.
The TENANT will pay $500 for each hour or its portion up to two (2) hours that the premises are occupied after the agreed check-out time, and $25 per lost key.
The Landlord will make every effort to ensure that equipment and appliances are in good working order and to have any repairs made in a timely manner but does not guarantee against appliance and equipment failure including but not limited to air conditioning, Internet, cable TV, dishwasher, washer, dryer or gas grill.
The Landlord is not responsible for lost or stolen items. The tenant agrees to pay return shipping and handling charges for any item left behind and requested for return after the end of the tenancy.
The tenant understands and accepts that the property may be protected with outside security cameras (e.g., Ring doorbell). These cameras are used to protect the property from potential break-ins and theft. Any attempt at disabling, redirecting, or obscuring the cameras is prohibited and may result in lease cancellation. There are no cameras activated inside the house.