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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 spacious living room with a blue sofa, wooden coffee table, and a fireplace. Large windows offer a view of the outdoors.
A modern living room with a large sliding glass door leading to an outdoor deck with a view of a lake.
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.

Reviews

10 out of 10
Exceptional

Highlights

  • Enjoy the heated pool
    A rare find in this area - swim in comfort or have a relaxing dip.
  • Discover nearby landmarks
    Walk to Orleans Bowling Center

Popular amenities

  • Spa pool on site
  • Private pool
  • Patio
  • Toys
  • Barbecue
  • Pet-friendly

Explore the area

View map
Orleans, MA
  • Place, Addison Art Gallery
    ‪2 min walk‬
  • Place, Cape Escape Adventure Golf
    ‪16 min walk‬
  • Place, Orleans Bowling Center
    ‪16 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

Add dates for prices

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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. Orleans Bowling Center and Cape Escape Adventure Golf are also worth visiting. Looking to get your feet wet? Kayaking, fishing and swimming adventures can be found near the property.
View more Holiday homes in OrleansOpens in a new window
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
  • Academy of Performing Arts - 3 min drive - 1.8 km

Getting around

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

Restaurants

  • ‪Hot Chocolate Sparrow - ‬6 min walk
  • ‪The Knack - ‬14 min walk
  • ‪Wendy's - ‬16 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 October 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 13 December 2026 start from NZ$18,785, 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 within 1 mile (2 km) of Addison Art Gallery, Orleans Bowling Center and Cape Escape Adventure Golf. Academy of Performing Arts and Church of the Transfiguration Orleans are also within 2 miles (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 16 out of 16 reviews
Rating 8 - Good. 0 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

10/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Tremendous property and layout. It's right near downtown, but it's very quiet / secluded and the three properties give everyone their own space. It's also a great, central location to explore the mid Outer Cape. Chatham, Wellfleet, Brewster are all 20 minutes away
Stayed 5 nights in Aug 2026
Response from VrboOwner on 31 August 2026
Hi Micah! Thanks so much for taking the time to write a review of your stay with us. And we are thrilled that you enjoyed your Pretty Picky Properties experience. The location is tough to beat! Hopefully we will see you again soon. Pretty Picky Properties Cape Cod's Select Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family reunion

Perfect place for large family reunion
Stayed 3 nights in May 2024
Response from VrboOwner on 4 June 2024
Hi Christopher! Thanks so much for taking the time to write a review of your stay with us. And we are thrilled that you enjoyed your Pretty Picky Properties experience. Hopefully we will see you again soon – be sure to check out our site for more Pretty Picky Properties. Pretty Picky Properties Cape Cod's Select Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great for large group! Beautiful House.

3 separate houses were great for our team offsite. Lots of space for everyone to hang out together. House is made for rentals and very well appointed. The management company was incredible helpful.
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This place is AMAZING. I wouldn't change a thing. If I could give it 100 stars, I would.
Stayed 3 nights in Oct 2025
Response from VrboOwner on 18 October 2025
Hi Susanne! Thanks so much for taking the time to write a review of your stay with us. And we are thrilled that you enjoyed your Pretty Picky Properties experience. We hope you had a wonderful birthday celebration! Hopefully we will see you again soon. Pretty Picky Properties Cape Cod's Select Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Experience

Amazing experience for my family of 23 staying at this beautiful estate. I asked everyone to give me their review of the property before I submitted mine online, and not one person had a single complaint. It fit my family perfectly, and we enjoyed every minute of it. From check-in to check-out, everything was seamless and easy.
Stayed 7 nights in Sep 2022
Response from VrboOwner on 1 October 2022
Hi Greg. Thanks so much for taking the time to write a review of your stay with us. And we are thrilled that you enjoyed your Pretty Picky Properties experience. We aim for seamless and easy for your vacation! Hopefully we will see you again next year – be sure to check out our site for more Pretty Picky Properties. Pretty Picky Properties Cape Cod's Select Vacation Rentals
Verified review

10/10 Excellent

Perfect Multi-Family Vacation Spot

We spent a week here with 6 families and their children, with ages ranging from 6 months to 10 years old. It would be difficult to find a more perfect spot for our group. Everyone enjoyed the pool and giant yard. The living areas of the main house provided a perfect rally point for breakfast, dinner, and evening cocktails. The outdoor kitchen gave us another spot to grill, play games and enjoy the views while keeping an eye on the little ones. The houses are completely stocked with kitchen gear, pool toys and towels, outdoor games, and sports equipment for land and water. There are restaurants, shops and grocery stores all within walking distance, but we couldn't pull ourselves away from the house for long. Our only complaint was that the week flew by way too fast and we all had to return to reality.
Stayed 7 nights in Aug 2018
Response from VrboOwner on 1 April 2020
Thanks so much for taking the time to write a review of your stay with us. And we are thrilled that you enjoyed your Pretty Picky Properties experience. Hopefully we will see you again next year – be sure to check out our site for more Pretty Picky Properties. Pretty Picky Properties Cape Cod's Select Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great family get together

We all had great fun at the property
Stayed 3 nights in Oct 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing stay !

My wife and I just had our wedding weekend here and everything was outstanding! We had 18 adults and 4 children and the house worked great for all! The pool was the star of the show and allowed for great mornings and fun nights. Unreal views and amenities to pair with a great location. Unbelievable spot for a classic Cape Cod vacation! Literally everybody was saying, "so family reunion here every summer?!?".
Stayed 4 nights in Sep 2021
Response from VrboOwner on 1 October 2021
Thanks so much for taking the time to write a review of your stay with us. And we are thrilled that you enjoyed your Pretty Picky Properties experience. Congrats - we hope to see you for your first anniversary! Hopefully we will see you again next year – be sure to check out our site for more Pretty Picky Properties. Pretty Picky Properties Cape Cod's Select Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing location for family reunion

Our extended family of 16 tries to get away for a family vacation every couple of years. We all agreed this was our best location yet. The pool is AMAZING and fully accommodates a crowd of kids and adults. We used the huge lawn for bocce, whiffle ball, and a game of capture the flag. The kayaks got used daily, and many of us tried paddle boarding for the first time. We gathered every night after dark by the fire pit. We had ages ranging from 8 to 80 and everyone had fun. There's plenty to space to hang and play together, but also enough space for people to get away when they wanted to be alone and read a book. We simply can't say enough - the place is perfect.
Stayed 7 nights in Aug 2021
Response from VrboOwner on 16 August 2021
Thanks so much for taking the time to write a review of your stay with us. And we are thrilled that you enjoyed your Pretty Picky Properties experience. We love to see "perfect" in our reviews! Hopefully we will see you again next year – be sure to check out our site for more Pretty Picky Properties. Pretty Picky Properties Cape Cod's Select Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

wedding

We had a group of us staying at the house following a wedding in Chatham. It was the perfect place for us to relax and enjoy our time away. We never left the house! It was perfect from the moment we unpacked the car. Looking forward to going back next year.
Stayed 7 nights in Jul 2021
Response from VrboOwner on 12 August 2021
Thanks so much for taking the time to write a review of your stay with us. And we are thrilled that you enjoyed your Pretty Picky Properties experience. It's always wonderful to see "perfect" in our reviews! Hopefully we will see you again next year – be sure to check out our site for more Pretty Picky Properties. Pretty Picky Properties Cape Cod's Select Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house

Excellent house with a lot of add ons. The music system, fire pit, pool, decore, kitchen equipment, and location made it memorable. its a 10 out of 10.
Stayed 8 nights in Jun 2021
Response from VrboOwner on 22 June 2021
Thanks so much for taking the time to write a review of your stay with us. And we are thrilled that you enjoyed your Pretty Picky Properties experience. You can't beat a 10 out of 10! Hopefully we will see you again next year – be sure to check out our site for more Pretty Picky Properties. Pretty Picky Properties Cape Cod's Select Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Property

Everything about the property was what we anticipated. The only issue we had was the pool was not heated which in the description it listed a heated pool. Fortunately the pool maintenance man happened to stop by and was able to turn on the pool heater.
Stayed 3 nights in May 2021
Response from VrboOwner on 1 June 2021
Thanks so much for taking the time to write a review of your stay with us. And we are thrilled that you enjoyed your Pretty Picky Properties experience. As stated in the listing description the pool is heated from Memorial Day to Columbus Day each season, but I'm glad they were able to get it on for you before Memorial Day this year. Hopefully we will see you again next year – be sure to check out our site for more Pretty Picky Properties. Pretty Picky Properties Cape Cod's Select Vacation Rentals
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, location, listing accuracy

loved it

This property is gorgeous! We loved every minute of our stay.
Stayed 4 nights in Sep 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing!

The house and stay was above and beyond our expectations, I would recommend the property to anyone.
Stayed 4 nights in Sep 2019
Archival

10/10 Excellent

Fantastic property.

Perfect place for a large group! We loved the pool and the fire pit. Fun for all ages!
Stayed 7 nights in Aug 2017
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 4 nights in May 2026
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