This vacation home places you within a short walk of Jonathan Young Windmill and within a mile (2 km) of Orleans Bowling Center. The vacation home includes a private pool, a kitchen, and a patio.
Hyannis, MA (HYA-Barnstable Municipal) - 30 min drive
Restaurants
Wendy's - 16 min walk
Hot Chocolate Sparrow - 6 min walk
The Knack - 13 min walk
Hog Island Beer Co. - 3 min drive
Cooke's Seafood - 6 min walk
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 $ 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 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! ℠
The vacation home is air-conditioned and features a kitchen, 10.5 bathrooms, and a patio, and there's space to spread out with 10 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a private pool, a washing machine, and a sofa bed.
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
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
This property welcomes pets
Service animals exempt from fees
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
Check-in: 4:00 PM
Check-out: 10:00 AM
Minimum check-in age: 25
Property Registration Number C0082492240
We should mention
Details about charges, deposits, or other important information:
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Onsite parties or group events are strictly prohibited.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.
Property is also known as
455229
Frequently asked questions
What can I see around this vacation home?
This vacation home is located in Orleans, a short 15-minute walk from Orleans Bowling Center and also 11 minutes on foot from Jonathan Young Windmill. You'll also find Cape Cod Beaches and Cape Cod National Seashore within a short drive.
Is parking available on site at this vacation home?
No, this vacation home doesn't offer parking.
Is this vacation home next to a casino?
No, this vacation home is not connected to a casino.
Will I find an indoor pool at this vacation home?
No, this vacation home doesn't have an indoor pool; however, there is a hot tub.
What will couples enjoy most about a stay at "Second Wind" :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24?
Amenities that appeal to couples at this waterfront vacation home include a private pool, a kitchen, and a smart TV.
Are there hot tubs at "Second Wind" :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24?
Yes, this vacation home has a spa tub.
Does this vacation home provide breakfast?
No, this vacation home doesn't offer breakfast.
Will this vacation home allow pets to stay free of charge?
Although pets can't stay for free, they are welcome at this vacation home.
Are there connecting rooms at this vacation home?
No, this vacation home doesn't feature connecting guestrooms.
How far is the airport from this vacation home?
The closest major airport to this vacation home is Hyannis, MA (HYA-Barnstable Municipal), which is 20.9 mi away (30 minutes by car). Another top airport is Provincetown, MA (PVC-Provincetown Municipal), which is located 28.6 mi away (45-minute drive).
Are there rooms with balconies at "Second Wind" :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24?
Yes, every accommodation at "Second Wind" :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24 comes with a deck with some featuring water views.
"Second Wind" :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24 Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers 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.
Rating 10 - Excellent. 13 out of 13 reviews
10 - Excellent
13
Rating 8 - Good. 0 out of 13 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 13 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 13 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 13 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
Millicent M.
Oct 29, 2024
Liked: Cleanliness
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
Christopher M.
Jun 3, 2024
Liked: Cleanliness
Family reunion
Perfect place for large family reunion
Christopher M.
Stayed 3 nights in May 2024
10/10 Excellent
Greg M.
Sep 29, 2022
Liked: Cleanliness
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
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
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
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
Traci C.
Jul 28, 2021
Liked: Cleanliness
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
Cristina F.
Jun 21, 2021
Liked: Cleanliness
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
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
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
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
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!