House in Orleans, MA

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

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

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

Welcome to "Second Wind"
Pretty stunning at night as well...
Heated pool
Unclassified image, 4 of 28, button
View of the Carriage house and Main House from the fire-pit area of the pool deck.

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

10 out of 10 Exceptional
10 bedrooms10+ bathroomsSleeps 24548 sq m

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly

Check out the area

Orleans, MA
  • Popular LocationRock Harbor Beach3 min drive
  • Popular LocationSkaket Beach6 min drive
  • Popular LocationNauset Beach6 min drive
  • AirportBoston, MA (BNH-Boston Harbor Seaplane Base)111 min drive

Rooms & beds

10 bedrooms (sleeps 24)

Guest Bedroom #1

1 King Bed

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

10 bathrooms, 1 half bathroom

Carriage House

Toilet · Shower only

Carriage House Primary Bathroom #1

Toilet · Shower only

Guest Bath Main House

Toilet · Shower only

Guest Bath Main House

Bathtub or shower · Toilet

Guest House

Toilet · Shower only

Guest House

Toilet · Shower only

Guest House - Primary Bathroom #4

Toilet · Shower only

Main House

Toilet · Shower only

Main House - Primary Bathroom #2

Toilet · Shower only

Power Room (2)

Toilet

Primary Bathroom #1

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Dining Area

About this property

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

This property is professionally managed by Pretty Picky Properties.

"Second Wind" - An Orleans Estate with large heated pool, 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

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 this site for more Pretty Picky Properties - your best selection of prime vacation homes available for summer rental on Cape Cod.

It's your vacation. Get Picky!

Property manager

Pretty Picky Properties
Premier Host
Premier Host

Languages

English

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Pet-friendly

House Rules

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

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

Pets allowed

Smoking

Smoking is not permitted

Damage and incidentals

You will be responsible for any damage to the rental property caused by you or your party during your stay.

Important information

You need to know

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
Safety features at this property include a carbon monoxide detector, a fire extinguisher and a smoke detector
Property registration number C0082492240

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 National Seashore and Cape Cod Beaches. Orleans Bowling Center and Edward Penniman House and Barn are also worth visiting. Discover the area's water adventures with fishing and swimming nearby, or enjoy the great outdoors with cycling.

What's nearby

  • Orleans Bowling Center - 15 min walk
  • Rock Harbor Beach - 3 min drive
  • Skaket Beach - 6 min drive
  • Nauset Beach - 6 min drive
  • Ocean Edge Golf Club - 8 min drive

Getting around

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

Restaurants

  • Wendy's - 16 min walk
  • Hot Chocolate Sparrow - 6 min walk
  • Rock Harbor Grill - 8 min walk
  • Dunkin' - 9 min walk
  • Papa Gino's - 12 min walk

Frequently asked questions

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

Yes, pets are allowed at this property.

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

Check-in begins at 4:00 PM.

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

Checkout is at 10:00 AM.

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

Situated on the waterfront, this holiday home is within 1 mile (2 km) of Jonathan Young Windmill and Orleans Bowling Center. Church of the Transfiguration Orleans and Rock Harbor Beach 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.
Learn moreOpens in a new window
Rating 10 - Excellent. 11 out of 11 reviews" "
Rating 8 - Good. 0 out of 11 reviews" "
Rating 6 - Okay. 0 out of 11 reviews" "
Rating 4 - Poor. 0 out of 11 reviews" "
Rating 2 - Terrible. 0 out of 11 reviews" "

10/10

Cleanliness

9.8/10

Check-in

9.6/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

10/10 Excellent

Greg M.

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

10/10 Excellent

Ehsan M.

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

10/10 Excellent

Tim P.

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

10/10 Excellent

Jeanne B., Reading, MA

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

10/10 Excellent

Traci C.

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

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

Languages:

English

Premier Host

Premier Host
They consistently provide great experiences for their guests
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