South Orleans Rentals USA Massachusetts Orleans South Orleans

Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly | Cottage in Orleans

9.6 (41 Reviews) |   Pet Friendly   4 Bedrooms  2 Bathrooms  8 Guests
South Orleans Cottage | Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly

4 Bedroom Cottage in South Orleans, Orleans

This updated 4-bedroom 2-bathroom home has the best view on Pleasant Bay, hands down. The open floor plan is ideal for large family gatherings, and conversations blend easily through two large sliders that open onto an expansive deck overlooking the Bay. This nautical-style "Old Cape Cod" cottage sleeps 8. Two waterfront bedrooms—one with a king bed and one with a queen bed—have commanding views of Pleasant Bay. A third bedroom on the second floor sleeps two in twin beds. A fourth bedroom on the first floor has a queen bed with an adjacent first floor bathroom.
Built in 1941, Square Top commands center stage near the Northern end of an historic 3.6-acre estate, and the water’s edge is literally a stone’s throw away. Enjoy your morning coffee and your evening meals on the rustic decks overlooking the Bay. Spend your vacation beach combing, exploring the Cape and learning to sail with Pleasant Bay Community Boating (PBCB) located on this expansive property.
*Summer guests (June 1-Sept 6) can enjoy a five individual sails on a Sunfish sailboat and unlimited kayak uses during your stay.
*This sweet cottage--named "Square Top"--has central AC, heat and wifi. The fireplace is decorative only, and cannot be used for fires--thanks!

Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly is located in South Orleans. Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly provides accommodation, featuring Air Conditioner, Parking, Barbecue/Outdoor Cooking, among other amenities. This Cottage features Air Conditioner, Parking, Barbecue/Outdoor Cooking, to make your stay a comfortable one.

Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly has 4 Bedrooms , 2 Bathrooms, and max occupancy of 8 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated Cottage because of the excellent services rendered by the owner or manager of this Cottage, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. Cottage has a friendly neighborhood, and the South Orleans has interesting places to visit. If you want to learn more about the Cottage in South Orleans, such as places to visit and things to do nearby, you can check below to learn more.

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Unique Amenities

  • Air Conditioner
  • Parking
  • Pet Friendly
  • TV
  • View
  • Ocean View
  • Balcony/Terrace
  • Oceanfront
  • Security/Safety
  • Sports/Activities
  • Bedding/Linens
  • Fireplace/Heating
  • Entertainment
  • Barbecue/Outdoor Cooking
  • Child Friendly
  • Internet
  • Kitchen
  • Laundry
 
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Policies

Event Policy No events allowed
Check-in Check-in time starts at 4:00 pm minimum check-in age: 25
Check-out Check-out before 9:30 am
Child Policy Children are welcome.
Pet Policy 1 total pets note from host: under supervision at all times, leashed outside. pets allowed service animals are welcome, and are exempt from fees welcoming dogs only
Smoking Policy Smoking is not permitted
Other Policy 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 host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip host has not indicated whether there is a smoke detector on the property onsite parties or group events are strictly prohibited property registration number c0163352240 special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
 
Orleans, 02662, United States

What Our Guests say 500 + Reviews

Oct 15, 2024 06:05:50 AM
Summary: Very clean. Would reckon it to everyone! Great time
Deborah C. Deborah C.
Sep 17, 2024 08:23:05 AM
Summary: This place was everything we could have wanted for a place to stay for a friend’s wedding. Spacious, well lit, comfortable beds. The deck is spacious and so peaceful to sit on and watch the sailors. It is a short drive to Chatham, Harwich, and Orleans. Kitchen had the essentials for cooking breakfast. Would definitely stay here again!
Emily R. Emily R.
Sep 7, 2024 03:13:52 AM
Summary: We had an amazing time, view and host.
John E. John E.
Aug 29, 2024 12:23:06 AM
Summary: The house was clean, pleasant, needs updating. Kitchen is older gally style. Your parking is in a short walk, but you can drop off in front of house. Property is part of community sailing camp. Beautiful view. We were given a sailing lesson which was great! Also can use kayaks a
Marilyn m. Marilyn m.
Aug 28, 2024 06:59:12 PM
Summary: Location is great. The view of the bay and the sailing club is amazing . The beach is modest at best , The house was comfortable and clean and the manager very helpful. The house is old fashioned but the living space and the porch is right on the bay and great. The breeze from the bay was delightful.
Susan N. Susan N.
Aug 14, 2024 12:32:58 AM
Summary: We stayed here for our wedding week and I couldn't have asked for a better place. Great spot to hang out and steps to the beach. Everything was perfect. thank you!
Jessica D. Jessica D.
Aug 5, 2024 10:29:42 PM
Summary: The cottage is adorable and had everything our family needed for a wonderful stay. The staff of Pleasant Bay Community Boating (our hosts) could not have been more helpful. The views are just beautiful.
Treseanne A. Treseanne A.
Jul 21, 2024 01:25:53 AM
Summary: We had an absolutely amazing week at this house. We were able to enjoy some sailing, fishing, kayaking, an amazing sunset. The views from each of the bedrooms are amazing. Property is also closely located to Orleans beaches that are amazing as well.
Jennifer R. Jennifer R.
Jul 13, 2024 09:15:11 PM
Summary: Close to a lot of great spots and loved being on the water. House was perfect for our group. We’ll be back for sure!
Jake P. Jake P.
May 28, 2024 08:45:24 PM
Summary: We had a wonderful, relaxing time- mostly on the big wrap-around deck overlooking the beautiful bay. The cottage was immaculate and we were even able to check in early! We were also very fortunate to have stayed when the majority of the time there were no events, otherwise the dock would have been very busy and we wouldn't have been able to park close to the cottage. The only real downside was finding that the refrigerator outlet didn't work- but we made do with an extension cord. Thank you very much for such an enjoyable stay!!
Kathy-Lee S. Kathy-Lee S.

FAQ's

Is this South Orleans cottage pet-friendly for guests?

Yes, pets are allowed at this property. Check the guest reviews to learn what guests had to share.

Does the South Orleans cottage have a swimming pool?

No, this South Orleans cottage does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in South Orleans cottage?

Best-rates for the South Orleans cottage starts from $878 per night with includes Air Conditioner, Parking, Barbecue/Outdoor Cooking, Child Friendly, Sports/Activities, Internet, TV, View, Ocean View, Oceanfront, Security/Safety, Bedding/Linens, Fireplace/Heating, Entertainment, Pet Friendly, Balcony/Terrace, Kitchen, Laundry StayAndPlay offers fully equipped golf villas, golf hotels, golf resorts, luxury golf cabins, and exclusive golf retreats, making it easier than ever to find your perfect golf escape — ideal for families, peaceful getaways, or pet-friendly retreats with the whole crew.

Is South Orleans cottage a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this cottage Good or guests have recommended them suitable for families. As reported by the owner or manager, the cottage has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the South Orleans cottage wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the South Orleans cottage has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the South Orleans cottage?

Based on the information reported by the owner or manager, the South Orleans cottage indicates 1 day stay policy at this cottage. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for South Orleans cottage?

Based on the information reported by the owner or manager, details for the cancellation policy for the South Orleans cottage are as follows: Cancellation policy Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.

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