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

Top rated by guests
Welcome to "Second Wind"
Here is the beautiful new kitchen
Island seating as well so you can watch the chef work their magic
Fully appointed kitchen with two refrigerators and two dishwashers - perfect for larger groups.
And a butlers pantry with a beverage refrigerator and wet bar
review stars
10.0Outstanding
(14 Ratings)
"This place is AMAZING. I wouldn't change a thing. If I could give it 100 stars, I would."
Susanne S.
Don't miss out! Price and availability may change
10.0 / 10.0
Outstanding(14 Ratings)

House in Orleans, MA

24 guests · 10 bedrooms · 10 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this house rental

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 $ 245.00. In addition, there are state and local taxes applied to all reservations less than 31 days in length that total 17.45%.

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! ®

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

Free WiFi/internet
Air conditioning
Pool
Non-smoking
Pets allowed
TV
Refridgerator
Kitchen
WiFi/Internet
Private pool access
Microwave
Dishwasher
Washing machine
Dryer
Patio
Oven
Stove
Laundry services
Bath or shower
Sofa bed
Ironing facilities
Towels
Hairdryer

Map of Orleans, MA


Ratings and reviews

10.0 / 10.0
Outstanding(14 Ratings)
10.0 / 10.0Outstanding·Oct 2025
This place is AMAZING. I wouldn't change a thing. If I could give it 100 stars, I would.
10.0 / 10.0Outstanding·Oct 2024
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.
10.0 / 10.0Outstanding·Jun 2024
Perfect place for large family reunion
10.0 / 10.0Outstanding·Sep 2022
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.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

Yes, a swimming pool is available for use at Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24. Enjoy the water!

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

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24?

We found 23 amenities for this rental. This includes free wifi/internet, air conditioning, pool, non-smoking, and pets allowed.


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