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Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24

Photo gallery for Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24

A modern living room with a blue sofa, a fireplace, and large windows offering a view of greenery.
A swimming pool with lounge chairs and umbrellas, surrounded by a landscaped garden and a large building in the background.
A modern kitchen with white cabinets, a central island with stools, stainless steel appliances, and pendant lighting.
A modern living room with a large sliding glass door leading to an outdoor deck with a view of a lake.
A spacious living room with a blue sofa, wooden coffee table, and a fireplace. Large windows offer a view of the outdoors.

Reviews

10 out of 10
Exceptional
Perched along the water, this vacation home features 10 bedrooms and 10 bathrooms, accommodating 24 guests. It includes 1 hot tub for relaxation. Guests enjoy swimming, kayaking, and fishing nearby. The property offers water views and a patio. It is pet-friendly and located near the Addison Art Gallery and Jonathan Young Windmill.

Highlights

  • Family fun awaits
    Top-rated for families.
  • Enjoy the heated pool
    A rare find in this area - swim in comfort or have a relaxing dip.
10 bedrooms10+ bathroomsSleeps 24

Popular amenities

  • Private pool
  • Spa pool on site
  • Onsite parking available
  • Pet-friendly
  • Kitchen
  • Washing machine

Explore the area

View map
Orleans, MA
  • Place, Jonathan Young Windmill
    ‪11 min walk‬
  • Place, Cape Escape Adventure Golf
    ‪16 min walk‬
  • Place, Orleans Historical Society Meeting House Museum
    ‪19 min walk‬
  • Airport, Hyannis, MA (HYA-Barnstable Municipal)
    ‪35 min drive‬

Rooms & beds

10 bedrooms (sleeps 24)

Guest Bedroom #2

1 Single Bed and 1 Queen Bed

Guest Bedroom #3

2 Single Beds

Guest Bedroom #5

2 Single Beds and 1 Queen Bed

Guest Bedroom #6

1 Queen Bed

Guest Bedroom #7

1 Single Bed, 1 Double Sofa Bed and 1 Single Bunk Bed

Primary Bedroom #1

1 King Bed

Primary Bedroom #2

1 King Bed

Primary Bedroom #3

1 King Bed

Primary Bedroom #4

1 King Bed

Primary Bedroom #5

1 King Bed

10 bathrooms, 1 half bathroom

Carriage House

Toilet · Shower only

Carriage House Primary Bathroom #1

Toilet · Shower only

Guest Bath Main House

Bathtub or shower · Toilet · Shower only

Guest House

Toilet · Shower only

Guest House

Toilet · Shower only

Guest House - Primary Bathroom #1

Toilet · Shower only

Main House

Toilet · Shower only

Main House - Primary Bathroom #3

Toilet · Shower only

Power Room (2)

Toilet

Primary Bath #2 Main House

Toilet · Shower only

Primary Bathroom #1

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Dining area

About this property

Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24

This property is professionally managed by Pretty Picky Properties.

"Second Wind" - An Orleans Estate with large heated pool, spa, on Town Cove

Sleeps 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

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 three 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 third primary suite 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 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 $ 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 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 this 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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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property Registration Number C0082492240
Property # 333045vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Orleans

Located in Orleans, this holiday home is on the waterfront. The area's natural beauty can be seen at Cape Cod Beaches and Cape Cod National Seashore. Cape Escape Adventure Golf and Edward Penniman House and Barn are also worth visiting. Looking to get your feet wet? Kayaking, fishing and swimming adventures can be found near the property.
Map
Orleans, MA

What's nearby

  • Addison Art Gallery - 2 min walk - 0.2 km
  • Jonathan Young Windmill - 11 min walk - 1.0 km
  • Cape Escape Adventure Golf - 16 min walk - 1.4 km
  • Orleans Bowling Center - 16 min walk - 1.4 km
  • Orleans Historical Society Meeting House Museum - 19 min walk - 1.7 km

Getting around

  • Hyannis Transportation Center - 32 min drive
  • Hyannis, MA (HYA-Barnstable Municipal) - 30 min drive

Restaurants

  • ‪Wendy's - ‬16 min walk
  • ‪The Knack - ‬14 min walk
  • ‪Hot Chocolate Sparrow - ‬6 min walk
  • ‪Bayzo's Pub at Ocean Edge Resort - ‬7 min drive
  • ‪Jo Mama's - ‬7 min walk

Frequently asked questions

Is Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24 pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24?

As of 31 Aug 2026, prices found for a 1-night stay for 2 adults at Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24 on 28 Sept 2026 start from AU$15,516, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24?

On-site parking is available at the property.

What time is check-in at Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24?

Check-in begins at 4:00 PM.

What time is check-out at Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24?

Checkout is at 10:00 AM.

Where is Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24 located?

Situated on the waterfront, this holiday home is 0.7 mi (1.1 km) from Orleans Historical Society Meeting House Museum and 2 mi (3.3 km) from Cape Cod Beaches. Cape Escape Adventure Golf and Rock Harbor Beach are also within 2 miles (3 km).

About the host

Hosted by Pretty Picky Properties

Host profile image
There are a lot of places to rent for a summer vacation on the Lower Cape. There are only a few Pretty Picky Properties. Most are directly on or very near the beach. Our homeowners love their properties, fastidiously maintain them, and expect guests to treat them accordingly. Our guests demand a prime location and a vacation experience that far exceeds the typical Cape summer rental.

When you spend a good amount of money for a perfect summer vacation, you want to be sure before you commit. That's why we take the time to carefully and completely answer all your questions by phone or email. If you can visit the Cape in advance, we'll be happy to show you one or more properties you're considering.

Most guests are also comforted to know that Pretty Picky also has a property management division. Most unforeseen property issues can be resolved quickly with our ready access to maintenance resources.

We look forward to helping you plan your ideal Cape Cod vacation!

The Pretty Picky Team

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