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

Orleans, Massachusetts
$5243 avg/night Minimum Stay 3 Nights
Bed 10

Bed

Bath 10

Bath

Home Private Vacation Home

Property Type

Sleep 24

Max Sleeps

Night 3 nights

Min Stay

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 forthe 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.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    10 Bedrooms Bed Sheets Provided Sofa Bed
  • GENERAL

    Unit Size: 5900 Sq Ft (548 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Kitchen Island Microwave Oven Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Patio
  • POOL/SPA

    Heated Pool Hot Tub Private Pool
  • BATHROOMS

    10.5 Bathrooms Hair Dryer Shower/tub Combination Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Fishing Nearby Kayak On Site Kayaking Nearby Swimming Nearby Whale Watching Nearby
  • ENTERTAINMENT

    Books Games Stereo Video Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Toys
  • LOCATION HIGHLIGHTS

    Near The Sea On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 24

Map Map

School District Rates & Availability

Review Review

  • Susanne S.

    Submitted Oct 15, 2025

    Stayed Oct 10, 2025

    This place is AMAZING. I wouldn't change a thing. If I could give it 100 stars, I would.

  • Millicent M.

    Submitted Oct 29, 2024

    Stayed Oct 15, 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.

  • Christopher M.

    Submitted Jun 3, 2024

    Stayed May 31, 2024

    Perfect place for large family reunion

  • Greg M.

    Submitted Sep 29, 2022

    Stayed Sep 17, 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.

  • Ehsan M.

    Submitted Oct 22, 2021

    Stayed Oct 8, 2021

    We all had great fun at the property

  • Tim P.

    Submitted Sep 26, 2021

    Stayed Sep 22, 2021

    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?!?.

  • Jeanne B.

    Submitted Aug 16, 2021

    Stayed Aug 8, 2021

    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.

  • Traci C.

    Submitted Jul 28, 2021

    Stayed Jul 18, 2021

    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.

  • Cristina F.

    Submitted Jun 21, 2021

    Stayed Jun 3, 2021

    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.

  • Carol U.

    Submitted May 31, 2021

    Stayed May 23, 2021

    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.

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Total

Includes taxes and fees
$5,243+
View details