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

TV, books
Iron/ironing board, free WiFi, bed sheets
Shower, towels
Iron/ironing board, free WiFi, bed sheets
Iron/ironing board, free WiFi, bed sheets

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 15-Sept 6) can enjoy a Simply Sail experience with one of our instructors at no charge (weather permitting)! Please reserve Simply Sail 1 month in advance through our website. *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 / Kitchenette
Internet / Wifi
Parking
Laundry
Balcony / Patio
Dishwasher
TV
Family friendly

Map of Orleans, MA

Cottage in Orleans, MA


Reasons to book

People love it hereGuests give this property a top rating
Great for pets
Includes essentialsPets allowed, Kitchen / Kitchenette, Air conditioner and more

$$$$

Reviews

4.6/5.0
Outstanding(31 Reviews)
4.0
star 5 empty
Aug 2023
This property was clean, airy and filled with light. The view of the Bay from the back of the house and deck was absolutely lovely. The house was complete in serving any kitchen, bathroom and living need we had for amenities. The central air conditioning was such relief given the unusual season of high humidity and little breeze from seaside locations. We found the property manager quick to respond to any queries we had and repairs that presented themselves. The only down side was parking off site which was an inconvenience since the Pleasant Bay Boating community used the parking in front of the cottage for parking or drop-off. Traffic and boat launch noise was at times aggravating. Overall, it did not put a dent in our overall enjoyment of this property.
5.0
Aug 2023
We had a great time at Square Top. It was so fun being right in the middle of all the action of the community boating program. Thanks!
5.0
Jul 2023
This comfortable cottage with stunning views was a perfect springboard to beautiful beaches, restaurants and more. We hope to return!
5.0
Jun 2023
The location with water access is unbeatable and conveniently located to downtown Orleans and Chatham (<10 min drive) if do decide want to leave the property. We also took a quick drive up to Wellfleet to explore. We would start our mornings bright and early down at the essentially private beach, our dog loved swimming and the shallow water allowed us to take our daughter swimming, paddle boarding and kayaking. A few other highlights:
4.0
star 5 empty
Sep 2022
Pretty view! Really appreciated the quick response time and accommodating spirit of property manager.
2.0
star 3 emptystar 4 emptystar 5 empty
Sep 2022
This property is centrally located on the Cape making it convenient to visit all areas of interest. Additionally, it’s location facing Pleasant Bay is absolutely breathtaking. There are kayaks and life vests, which we did not take advantage of, however the steps to the beach area were a bit treacherous. There is also a grill which we also did not use. But… renters beware. The photos belie the actual premises. This house has incredible potential, but sadly it’s been very neglected. Many of the areas are in dire need of updating. While my party of 4 were mostly comfortable in our bedrooms, there was nothing inviting about our rooms. Linens were aged and clearly overused. The kitchen was old fashioned, which we found charming on-line, was very run down all around. Three bathrooms were advertised, but there are only two and the one on the first floor has only a prefab stall shower. All of the fixtures in the bathroom were very outdated and many were rusted. Electrical outlets and lighting was questionable, as well as the plumbing. We enjoyed the back deck but it was also in need of a good cleaning and repairs in some places. The patio furniture was old, rusty and worn. The house could have been cleaner. Mismatched chairs and linens. A plethora of mismatched floor rugs, bent screen doors, lighting fixtures with pull chains that were missing strings, no outlet in the upstairs bathroom, blinds without operating cords, no bathroom amenities whatsoever other than tp. Additionally, the entrance to the house is up a concrete flight of stairs over a rickety flagstone path. We would not consider this wheelchair accessible. In short, the house reminds one of a shore house that college students might rent for summer vacation. It is very run down. Parking, while “on property” is at least 200 feet away and information regarding checking in was confusing at best. While there were visitor pamphlets in the dining area, more local info would have been welcomed. There is good Wi-Fi and tv service. Water was hot and pressure in the showers was good. The a/c seems to be acceptable also. We contacted the property manager with our concerns and to his credit we were refunded one nights stay and given a bottle of wine for our trouble. That was very nice, but it did not go far enough to entice us to return. We enjoyed our Cape stay, but we’re disappointed in what we felt were misrepresentations. We won’t be coming back..
4.0
star 5 empty
Sep 2022
All the big stuff about this house is great -- superb setting, light and airy rooms, good beds, hot shower, responsive manager. But the experience was diminished a bit by unnecessary small staff - nonfunctional and misshapen shades in the front bedrooms, moldy shower mats, broken chair in the side yard, light pulls that were frayed or too short. Once these are fixed, it will be 110% perfect!
5.0
Aug 2022
We had a lovely stay

FAQs

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

The average price for a rental in Orleans is $372 per night. This rental is $357 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 / kitchenette, internet / wifi, and parking.

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