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Newly renovated kitchen! Private cottage in great location with path to beach.

Bedrooms 2
Space sq. ft.
Property type cottage
Minimum Stay 5 nights


About the property

Cottage, 2 Bedrooms + Convertible bed(s), 2 baths, (Sleeps 4-6)

Molly’s Cottage is located in upscale Chocolate Hole, a great neighborhood for walking and running. It is a ten-minute drive to the spectacular National Park beaches and a few minutes away from the town of Cruz Bay (“Love City” has wonderful restaurants and shops).

Our cottage, made of tropical hardwoods, was lovingly built and maintained by our family over the past 20 years. We (a Vermont artist and her husband) have paid attention to detail in furnishings, art, and landscaping. We have just renovated the whole upstairs putting in a new larger kitchen. The kitchen is fully equipped. You can dine at home on the spacious deck overlooking Chocolate Hole beach. Relax and enjoy movies on a wide screen TV or simply take in the tropical night sounds

Molly’s Cottage is perfect for a couple that want an affordable and private small house, you can rent just the upstairs or both floors and share it with friends. The spacious bedroom and bath on the lower level is also perfect for a small family – put the kids downstairs and everyone has privacy.

Keywords: Cottage

More Details

Mary O'Shea
Member since: 2010
Speaks: english
Response time:
Within a few hours
Response rate:
Calendar last updated:
March 28, 2017

About Mary O'Shea

A Vermont artist and her husband

Mary O'Shea purchased this cottage in 1988

Why Mary O'Shea chose Cruz Bay

The cottage was built on family land but later sub-divided into its own property. We built this house ourselves and we take loving care of it.

What makes this cottage unique

The downstairs is separate and private. It is perfect for 2 couples or a small family because everyone gets privacy. We have a path that leads down to Chocolate hole beach. We are in a great area for walking and running. We always get a great breeze.


Estate Chocolate Hole and Great Cruz Bay Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
House Rules:
  • Max. occupancy 6
  • non smoking only
  • pets not allowed
  • Minimum Age Limit for Renters ...
Location Type:
  • Beach View
  • Ocean View
  • Away From It All
  • Budget
  • Family
  • Romantic
  • Clothes Dryer
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Parking
  • Parking Off Street
  • Telephone
  • Towels Provided
  • Washing Machine
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Dining Area
  • 2 Bathrooms
  • Bathroom 1 - toilet , shower
    Bathroom 1 - toilet , shower
  • 2 Bedrooms, Sleeps 6
  • Bedroom 2 - 1 queen , 1 twin/ single , 1 sleep sofa /futon
  • Queen size Beds (1), Double Beds (1), Twin or Single Beds (1), Sleep Sofa or Futons (1)
  • Books
  • CD Player
  • DVD Player
  • Games
  • Satellite / Cable
  • Stereo
  • Television
  • Balcony
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • restaurants
  • ruins
Leisure Activities:
  • beachcombing
  • boating
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • laundromat
Sports & Adventure Activities:
  • deepsea fishing
  • fishing
  • hiking
  • jet skiing
  • kayaking
  • parasailing
  • sailing
  • snorkeling
  • snorkeling/diving
  • swimming
  • tennis
  • wind-surfing


Exceptional! 5/5 -
(8 traveler reviews)

Newly renovated kitchen! Private cottage in great location with path to beach.
average rating of 5.0 based on 8 reviews
Jupiter, FL

Lovely Island Cottage

  • 5 of 5

My boyfriend and I visit St John fairly often, and we don't think of the island as a luxury destination - what keeps drawing us back is the simplicity of island life. We enjoy having a place to call home while we're there, and home is exactly what Molly's Cottage felt like when we stayed there last month. Cozy and tastefully decorated, with a great new open concept kitchen. We loved the large screened doors which let in the sunlight, cool breezes, and beautiful views (while keeping out the bugs!). Close to town without being right in it, and convenient to every part of the island. (Definitely recommend renting a jeep to get around and explore this amazing island!). Dining options on St John are excellent, but it was nice to enjoy some dinners at the cottage, too. There are several markets in town, so it's easy to stop and pick up whatever you need on your way back from the beach. The deck overlooking Chocolate Hole Bay is great - we ate breakfast there every morning, and it was the perfect place to relax with a cocktail or a glass of wine after days filled with hiking, paddle boarding, and beach bumming (be sure to use bug spray in the late afternoon/early evening when the no see ums and mosquitoes are fierce!). Being able to walk to the beach was fun - Chocolate Hole isn't the most spectacular beach on the island, but it was so nice to have it right there. Nice strolls in the morning and before dinner, and we did spend one very pleasant afternoon there swimming and beachcombing.

The lack of AC was not a problem thanks to the breezes and fans (who wants to listen to a noisy window AC unit anyway - or sleep with the windows closed - when you can be lulled to sleep by the sound of tree frogs, crickets, birds, and waves?!). Having a washer and dryer was convenient. We mostly used the clothes line for drying - those breezes dry laundry in no time! There is good internet connection at the cottage, too.

The owner is a pleasure to communicate with, quick to respond to emails and answer questions. We would definitely rent Molly's Cottage again. And we would certainly recommend it to anyone looking for a simple, laid back island experience.

  • Submitted: May 13, 2016
  • Stayed: Apr 2016
  • Source: VRBO, from HomeAway
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1 0
Portland Maine

Perfect Cottage

  • 5 of 5

We stayed at Molly's Cottage for a week at the beginning of March. It was clean, cozy, wonderfully decorated and a beautiful view. We had a great week. I was a little worried about not having AC but there was a constant breeze in the cottage and leaving all the doors open was just perfect. As a matter of fact, we needed a blanket at night because it got chilly at night! Natural breeze beats AC any day! I would definitely recommend this cottage and would rent here again.

  • Submitted: Mar 12, 2015
  • Stayed: Feb 2015
  • Source: VRBO, from HomeAway
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1 0

Delightful Cottage

  • 5 of 5

We loved our stay at Molly's cottage. It is evident that this home has been lovingly constructed and cared for. It is well maintained and super clean! It is charming in every way. We loved the deck and it's views. We ate our breakfast there every morning. It was very convenient to town as well. We would definitely rent this property again.

  • Submitted: Mar 18, 2014
  • Stayed: Mar 2014
  • Source: VRBO, from HomeAway
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2 0
Palatka, Florida

A Just Right Place

  • 5 of 5

Just right is how I can describe Molly's Cottage. We are not fancy, sophisticated folks and Molly's fit the bill Just Right - just the right size, just the right view and area - A Just Right place and time. Molly's was more than comfortable without A/C - A/C would have spoiled the fresh air and breeze. It was April and we were pulling up the blanket half way through the night. Molly's lacks only an internet connection, but being without it gave us time to read and get ready for the beach and adventuring.

The on-island host was available when we wanted and the owners corresponded quickly, especially since this trip was not finalize until about 60 days prior to departure.

Molly's Cottage was Just Right.

  • Submitted: May 4, 2013
  • Stayed: Apr 2013
  • Source: VRBO, from HomeAway
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3 0
Myrtle Beach, South Carolina

Cozy, comfortable cottage

  • 5 of 5

We just had a wonderful stay at Molly's cottage. Very tranquil setting with beautiful sunrises and sunsets, and ocean breezes that ensure a blissful night's rest. Enjoyed the beach in Chocolate Hole -found great shells and beautiful sea glass on our daily walks. If your looking for exciting nightlife, the town of Cruz Bay is nearby. We booked Cruz Bay excursions at the Westin, which is located within walking distance (good alternative if you don't have a car since the boat excursions leave from there at 745am) All in all, a very relaxing and memorable stay.

  • Submitted: Mar 24, 2013
  • Stayed: Mar 2013
  • Source: VRBO, from HomeAway
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3 0
Dallas, Texas

Perfect Weather

  • 5 of 5

What a great intimate cottage! We just got back and we already miss the amazing views, along with the cool breezes. Molly's Cottage was the perfect size for the two of us, never felt like we were cramped. The cottage has large doors that open (with screens) to keep the pesky mosquitoes at bay. We opened them every night around 6 p.m. and kept them open all night long, until we left to explore the island. The views are amazing of Chocolate Hole Bay and Chocolate Hole Pond. The sun rises were great to see, right from bed. We really loved the wrap around covered porch. Lots of meals and card games happened on that porch!

We grilled out almost every day on the porch, the kitchen is perfect, large fridge, lots of pots and pans, spices, etc. The neighborhood is great for running, walking and the walk down to the beach at Chocolate Hole is only 5 minutes and goes directly from the back porch to the beach. It's a bit of climb back out, but it's really not bad. Beware of the No-See-Ums gnat like bugs around 5:30 p.m., they will eat you alive on the the beach.

A few things to note and they aren't bad, just to keep in mind. The house is situated in a great neighborhood with other rentals, but also locals live there too. The house directly under us, you can only see a bit of the roof, is owned by a local. We know that life goes on and they can't tip toe around the renters, but on the third day we were there, their dog barked constantly throughout the night. The dog might as well have been in bed with us, it was so loud. The next morning, they were weed eating at 7 a.m. and that continued most of the morning. We returned home to a manure smell rising from their property. They loved their music and played it loud, but only occasionally. You might say, just go inside and shut all the doors. But that brings me to my next note.

Air conditioning. There is none. We found out very quickly, and rather warmly the night we arrived. The house had been shuttered all day, it was hot and muggy inside the cottage. Ceiling fans, stand up fans and keeping the doors open during the coolest parts of the day is a necessity. The first few days were an adjustment, but we actually really liked it. It forced us to spend time outside and really enjoy Chocolate Hole, instead of being cooped up indoors.

We would stay here again! We truly recommend it. Thanks so much for the letting us into your little slice of heaven!

  • Submitted: Jul 27, 2011
  • Stayed: Jul 2011
  • Source: VRBO, from HomeAway
Owner's Response: Thanks for the review! That is good advice about the no-see-ums not only on the beach but at the cottage also. We are glad you enjoyed your stay but I do have a couple of comments regarding the air conditioning and the neighborhood. When we built Molly’s Cottage twenty years ago we made a deliberate choice to avoid glass and air conditioning – hence the storm doors and screens. We wanted to take advantage of sea breezes for cooling and to that end we keep most of the shutters open whenever we are at home. Our choice is to keep the shutters open and use the ceiling fans when necessary to create a breeze. This results in less demand on the island’s sometimes-tenuous electric grid and generally reduces our footprint. While not true for every spot on the island, our cottage is situated so that there is almost always a great breeze. Our neighborhood is a mixed group of full time residents, vacationers, and part-timers, both West Indian and continental. As such there sometimes be some cultural clash around noise, pets, language, etc. The cultures are different and we try to respect these differences, while attempting to be good neighbors. We can only hope others will do the same.
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Rates & Availability

Estate Chocolate Hole and Great Cruz Bay Cottage Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly * Event
In Season
Jan 1 2017 - Apr 16 2017
5 night minimum stay
Notes: Rates are based on 2 guests; add $35 per night, per additional guest
Dec 18 2017 - Jan 3 2018
5 night minimum stay
Notes: Rates are based on 2 guests; add $35 per night, per additional guest
My Standard Rate
5 night minimum stay
Notes: Rates are based on 2 guests; add $35 per night, per additional guest

Additional information about rental rates

Tax Rate 12.5%

Owner's Cancellation Policy

Please ask the owner or check their rental agreement when booking the property.

Enter dates for accurate pricing

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We are a short walk to Chocolate hole beach and the Weston beach. A short ride to downtown and the North Shore beaches


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