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Second Wind :039-O An Orleans Estate with large heated pool, spa, on Town Cove; sleeps 24
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Reviews
10 out of 10, Loved by Guests
Top 10% based on
10 bedrooms10+ bathroomsSleeps 24548.1 sq m
Popular amenities
Explore the area

Orleans, MA
- Place, Addison Art Gallery2 min walk
- Place, Orleans Bowling Center16 min walk
- Place, Cape Cod Beaches3 min drive
- Airport, Hyannis, MA (HYA-Barnstable Municipal)29 min drive
Rooms & beds
10 bedrooms (sleeps 24)
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
Primary Bedroom #5
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 House
Toilet · Shower only
Guest House
Toilet · Shower only
Guest House - Primary Bathroom #1
Toilet · Shower only
Main House
Toilet · Shower only
Main House - Primary Bathroom #3
Toilet · Shower only
Power Room (2)
Toilet
Primary Bath #2 Main House
Toilet · Shower only
Primary Bathroom #1
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Dining area
About this property
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 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! ®
"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! ®
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Pet-friendly
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10.0 out of 10, Exceptional, (12 reviews)
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
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
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
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 Beaches and Cape Cod National Seashore. Orleans Bowling Center and Cape Escape Adventure Golf are also worth visiting. Looking to get your feet wet? Kayaking, fishing and swimming adventures can be found near the property.

Orleans, MA
What's nearby
- Addison Art Gallery - 2 min walk - 0.2 km
- French Cable Station Museum - 2 min walk - 0.2 km
- Cape Escape Adventure Golf - 14 min walk - 1.2 km
- Orleans Bowling Center - 16 min walk - 1.4 km
- Cape Cod Beaches - 3 min drive - 2.1 km
Getting around
Restaurants
- Wendy's - 15 min walk
- Hot Chocolate Sparrow - 6 min walk
- Dunkin' - 9 min walk
- Hog Island Beer Co. - 3 min drive
- Town Cove Tap House - 6 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
9.8/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
Verified
15 October 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Oct 2025
Verified
10/10 Excellent
Christopher M.
3 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family reunion
Christopher M.
Stayed 3 nights in May 2024
Verified
10/10 Excellent
Millicent M.
29 October 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great for large group! Beautiful House.
Millicent M.
Stayed 3 nights in Oct 2024
Verified
10/10 Excellent
Traci C.
28 July 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
wedding
Traci C.
Stayed 7 nights in Jul 2021
Verified
10/10 Excellent
Greg M.
29 September 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Experience
Greg M.
Stayed 7 nights in Sep 2022
Verified
10/10 Excellent
Chris K.
29 August 2018
Perfect Multi-Family Vacation Spot
Chris K.
Stayed 7 nights in Aug 2018
Verified
10/10 Excellent
Ehsan M.
22 October 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great family get together
Ehsan M.
Stayed 3 nights in Oct 2021
Verified
10/10 Excellent
Tim P.
26 September 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing stay !
Tim P.
Stayed 4 nights in Sep 2021
Verified
10/10 Excellent
Jeanne B.
16 August 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing location for family reunion
Jeanne B.
Stayed 7 nights in Aug 2021
Verified
10/10 Excellent
Cristina F.
21 June 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house
Cristina F.
Stayed 8 nights in Jun 2021
Verified
10/10 Excellent
Carol U.
31 May 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful Property
Carol U.
Stayed 3 nights in May 2021
Verified
10/10 Excellent
Kelly F.
23 September 2020
Liked: Cleanliness, check-in, location, listing accuracy
loved it
Kelly F.
Stayed 4 nights in Sep 2020
Verified
10/10 Excellent
Rosemara H.
18 September 2019
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing!
Rosemara H.
Stayed 4 nights in Sep 2019
Archival
10/10 Excellent
Peggi and Fred C.
21 August 2017
Fantastic property.
Peggi and Fred C.
Stayed 7 nights in Aug 2017
About the host
Hosted by Pretty Picky Properties
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
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
They consistently provide great experiences for their guests
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