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

Interior
Interior
Interior
Outdoor dining
Exterior
9.6
Outstanding(40 Reviews)

Cottage in Orleans, MA

8 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceOne of the higher cost properties in the area

About this cottage rental

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!

Amenities

Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Family friendly

Map of Orleans, MA

££££
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Reviews

9.6
Outstanding(40 Reviews)
10.0
Sep 2024
We had an amazing time, view and host.
8.0
Aug 2024
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
10.0
Aug 2024
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.
10.0
Aug 2024
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!
10.0
Aug 2024
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.
10.0
Jul 2024
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.
10.0
Jul 2024
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!
10.0
May 2024
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!!

FAQs

How much does this cottage cost compared to others in Orleans?

The average price for a rental in Orleans is £327 per night. This rental is £378 above the average.

Is parking included with this cottage?

Yes, parking is listed as an amenity at Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly. For more information, we encourage you to contact the property about where to park.

Is there a pool at this cottage?

We didn’t find pool listed as an amenity for this cottage. It may be worth double checking if a pool is important for your stay.

Is Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly pet friendly?

Yes! This cottage is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly?

We found 10 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and parking.

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