[See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # "Second Wind" :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24 Waterfront vacation home with private pool and kitchen ![A heated pool](https://images.trvl-media.com/lodging/34000000/33710000/33705900/33705838/bd69a1a8.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Smart TV, video games, books, stereo](https://images.trvl-media.com/lodging/34000000/33710000/33705900/33705838/1aa0c78a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33710000/33705900/33705838/414f253a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33710000/33705900/33705838/2ff4ac31.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33705900/33705838/4650cd88.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location In the heart of Orleans Village, Second Wind offers a tranquil retreat on picturesque Town Cove. Bring the whole family and spend hours around the heated pool, spa, and outdoor kitchen with fire pit. Walk to village shops and restaurants or explore Nauset Cove by kayak or boat. 10 Exceptional ### Entire home 10 bedrooms11 bathroomsSleeps 245900 sq ft ## Popular amenities - Parking available - Dryer - Pet-friendly - Hot tub - Washer - Pool ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### "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 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 $ 245.00 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 the Pretty Picky site for your best selection of prime vacation homes available for summer rental on Cape Cod. It's your vacation. Get Picky! ℠ ## Property amenities ### Pool/Spa - Heated pool - Hot tub - Private pool ### Internet - Available in the house: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Microwave - Oven - Refrigerator - Spices - Stovetop - Toaster ### Bedrooms - 10 bedrooms - Bedsheets provided - Sofa bed ### Bathroom - 10.5 bathrooms - Bathtub or shower - Hair dryer - Shower - Towels provided ### Living spaces - Living room ### Entertainment - Books - Games - Smart TV with cable/satellite channels - Stereo - Video games ### Outdoor areas - Barbecue grill - Patio ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - Pet friendly ### Suitability/Accessibility - Smoking not allowed ### Location highlights - Near the sea - On the waterfront ### Things to do - Heated pool - Kayak - Cycling nearby - Fishing nearby - Swimming nearby - Whale watching nearby ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) - Fire extinguisher ### General - Property located in a resort - Unit size: 5,900 square feet ## Similar properties ![Outdoor dining](https://images.trvl-media.com/lodging/72000000/71780000/71778600/71778590/85e6fd53.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Downtown Chatham Luxury 9 BR Home with Heated Pool. 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Telsa charge Orleans - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 14 reviews CA $2,274 CA $3,950 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-16&endDate=2025-10-17&selected=77960841&PinnedHotelID=77960841&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor dining](https://images.trvl-media.com/lodging/20000000/20000000/19994600/19994502/07b0cd4c.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Executive Waterfront Luxury Estate 6000 Sqft; Heated Pool; Elevator East Orleans - Ocean view - Pool - Kitchen - Washer 10 Exceptional 41 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&selected=19994502&PinnedHotelID=19994502&HadPinnedHotel=true®ionId=-1&adults=2) ![A heated pool](https://images.trvl-media.com/lodging/91000000/90320000/90313300/90313280/aa5f414a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Gables: 364-C Chatham Resort Style Estate with Heated Pool, Close to Everything Chatham - Pool - Hot tub - Kitchen - Washer 10 Exceptional 12 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30&selected=90313280&PinnedHotelID=90313280&HadPinnedHotel=true®ionId=-1&adults=2) ## Policies ### Check-in Check-in time starts at 4:00 PM Contactless check-in available Minimum check-in age: 25 ### Check-out Check-out before 10:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Pets Pets allowed Service animals are welcome, and are exempt from fees ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## 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 Onsite parties or group events are strictly prohibited Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property Safety features at this property include a fire extinguisher This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation Property Registration Number C0082492240 ### Property is also known as 455229 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C41.78813%2C-69.98820&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=TUpOJxS2W24L3qKrUba95Hz5LW0=) Orleans, MA #### What's nearby - Rock Harbor Beach - 3 min drive - 2.1 km - Nickerson State Park - 4 min drive - 4.3 km - Skaket Beach - 4 min drive - 2.9 km - Ocean Edge Golf Club - 8 min drive - 7.5 km - Nauset Beach - 9 min drive - 6.1 km #### Getting around - Hyannis Transportation Center - 32 min drive - Hyannis, MA (HYA-Barnstable Municipal) - 30 min drive #### Restaurants - ‪Wendy's - ‬15 min walk - ‪Hot Chocolate Sparrow - ‬6 min walk - ‪Dunkin' - ‬9 min walk - ‪The Knack - ‬14 min walk - ‪Cooke's Seafood - ‬6 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. ### 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? > Check-out 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 vacation home is 0.8 mi (1.3 km) from Orleans Bowling Center and within 3 mi (5 km) of Rock Harbor Beach and Skaket Beach. Nickerson State Park and Edward Penniman House and Barn are also within 3 mi (5 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## "Second Wind" :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24 Reviews 10 ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.[More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 13 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10/10 Cleanliness ### 10/10 Excellent #### Christopher M. Jun 3, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Family reunion Perfect place for large family reunion ##### Christopher M. Stayed 3 nights in May 2024 ### 10/10 Excellent #### Millicent M. Oct 29, 2024 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. ##### Millicent M. Stayed 3 nights in Oct 2024 ### 10/10 Excellent #### Traci C. Jul 28, 2021 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. ##### Traci C. Stayed 7 nights in Jul 2021 ### 10/10 Excellent #### Greg M. Sep 29, 2022 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. ##### Greg M. Stayed 7 nights in Sep 2022 ### 10/10 Excellent #### Ehsan M. Oct 22, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great family get together We all had great fun at the property ##### Ehsan M. Stayed 3 nights in Oct 2021 ### 10/10 Excellent #### Tim P. Sep 26, 2021 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?!?". ##### Tim P. Stayed 4 nights in Sep 2021 ### 10/10 Excellent #### Jeanne B., Reading, MA Aug 16, 2021 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. ##### Jeanne B. Stayed 7 nights in Aug 2021 ### 10/10 Excellent #### Cristina F. Jun 21, 2021 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. ##### Cristina F. Stayed 8 nights in Jun 2021 ### 10/10 Excellent #### Carol U. May 31, 2021 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. ##### Carol U. Stayed 3 nights in May 2021 ### 10/10 Excellent #### Kelly F. Sep 23, 2020 Liked: Cleanliness, check-in, location, listing accuracy #### loved it This property is gorgeous! We loved every minute of our stay. ##### Kelly F. Stayed 4 nights in Sep 2020 ### 10/10 Excellent #### Rosemara H. Sep 18, 2019 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. ##### Rosemara H. Stayed 4 nights in Sep 2019 ### 10/10 Excellent #### Chris K. Aug 29, 2018 #### 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. ##### Chris K. Stayed 7 nights in Aug 2018 This review was submitted before 2018 and has not been verified. ### 10/10 Excellent #### Peggi and Fred C. Aug 21, 2017 #### Fantastic property. Perfect place for a large group! We loved the pool and the fire pit. Fun for all ages! ##### Peggi and Fred C. 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