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Dorothy Billings

Member since: 2012
Call Owner
Speaks English

Private Waterfront Garden Cottage

Bedrooms 1
Property type cottage
Minimum Stay 3 nights


Photos and Description of this 1 bedroom holiday cottage in Bermuda - Oyster Point Guest Cottage

Cottage, 1 Bedroom + single sleep sofa, rollaway bed, crib, 1 Bath, (Sleeps 4


Oyster Point Cottage is located in a quiet neighborhood on the water’s edge in Southampton. It is within walking distance to several beaches, restaurants and pubs, pedestrian hiking trails along the old railway tracks, jet ski rentals, Gibbs Hill Lighthouse, spa facilities at the nearby Fairmont Southampton Princess and The Reefs, several golf courses including Port Royal, Riddell’s Bay and a short course at The Fairmont Southampton Princess. Grocery stores and the city of Hamilton, by vehicle, are only 5 minutes (15 minutes walk) and 20 minutes drive away respectively and bus stops are located at the end of the driveway to the cottage.

Cottage Interior:

The cottage includes a full kitchen, queen bedroom with walk in closet and bathroom en suite, living room with dining area and porch looking out at the bay and a wonderful vista of our beautiful Bermuda sunsets. Two rollaway bed and crib can be provided.


Small private beach with loungers and thatched umbrella, hot tub, sauna, dock and a kayak. Cable television, DVD and CD players, WiFi internet access, telephones (free local calls), AC usage, standing and ceiling fans.

The kitchen is fully equipped with refrigerator/freezer, microwave, electric stove, toaster oven, coffee maker, china, glassware, cutlery and cookware.

Bed linen, bath and beach towels, iron and board, travel crib and rollaway bed are all provided as well as a gas BBQ and chiminea situated on a covered porch with outdoor table, chairs and loungers.

A discounted rate is offered to our visitors on the charter sailing yacht “Bright Star 11” , a 55 ft. sailing yacht, which is owned by The Oyster Point Yacht Charters Ltd.

Keywords: charming, waterfront, cottage, self contained, charming, private, water activities, near beaches

More Details
  • children welcome
  • non smoking only
  • pets not allowed
  • wheelchair accessible
Dorothy Billings (Owner)
Member since: 2012
Call Owner
Speaks English

About Dorothy Billings

Our home is on the property but separate from the cottage. We have raised two adult children here.

Until last year our elderly mother lived in our cottage enjoying her independence while having family nearby. She lived until she was 92 but sadly she passed away last year.

We are local residents and would be happy to assist our guests in any way we can including old folk lore stories about the Island, directions and advice about interesting features, attractions, restaurants and anything else about Bermuda.

Dorothy Billings purchased this cottage in 1985

What makes this cottage unique

Friendly safe neighborhood, privacy, water's edge at the cottage door step, large grass lawn and garden, close to restaurants, pubs, grocery stores and other activities.

Guestbook comments from the owner

We are sad to be leaving – we loved this place and the Islands of Bermuda. Highlights for us were kayaking, travelling along the island roads on the local buses, swimming off the private beach whenever the urge took us and long sunsets on the terace with dark & stormies in hand. Brian and Dorothy were perfect hosts, ferrying us to the market and up to the lighthouse – our favorite dining spot on the island. We hope to return.
Aug 2014
  • 1 of 39


based on 22 holidaymaker reviews

Private Waterfront Garden Cottage
average rating of 4.8636365 based on 61 reviews

Anniversary celebration

  • 4 of 5

We just spent a week in this lovely cottage to celebrate our 55th Anniversary. Our last visit to Bermuda was in 1979 so it had been a long time since we were there. It has changed quite a bit! We did very much enjoy coming back each day to the cottage instead of a hotel room. There is nothing new to say - every review says it all!!

We enjoyed our Anniversary dinner at The Waterlot!! Very, very nice! Great that we could walk there. We rented a scooter for a few days. Roads are very busy and narrow! The weather was really not suitable for swimming which we were disappointed in. Thanks for sharing your great spot with us Dorothy and Brian.

Pat and Gene Hall

Sunapee, NH

  • Review Submitted: Oct 30, 2015
  • Date of Stay: Oct 2015
  • Source: VRBO, from HomeAway
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  • 5 of 5

This was my 4th visit to Oyster Point Cottage, and each time it becomes even more magical! There is nothing that Brian and Dorothy do not think of, if one has any questions, they are answered instantly, help is always at hand, especially from Abbie and Zoe(!) the cottage is just perfect, in the most wonderful position, as a single woman, I feel totally safe and at ease, and I cannot wait to go back again next year, to watch the sunrise from my early morning swim, to the sunset from the patio! It is such an easy place to get around from as well, I just love it, and if you have the time, you can wile away many hours just watching the boats on the water. I cannot think of a more perfect place to be. Brian and Dorothy, thank you again for your wonderful and thoughtful hospitality.

  • Review Submitted: Sep 12, 2015
  • Date of Stay: Aug 2015
  • Source: VRBO, from HomeAway
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2nd Honeymoon Haven

  • 5 of 5

My husband and I just returned from a week's stay at Oyster Point and we agreed it was ideal for our 10th anniversary vacation. I am still daydreaming about our meals and cocktails on the waterfront patio and the lovely view of Gibb's Lighthouse on the hill across from the cottage. We needed some peace and quiet and just a relaxing break from a busy life; this was the perfect place! Private beach on the property, use of a great kayak to explore the coves and lovely scenery and just a short walk from bus and trolley. If you golf, how can you not tee off at Port Royal and the Mid Ocean Club? Fantastic courses with ocean scenery that matches any others! Dorothy and Brian were a treasure of information about the island history and recommended places to eat/visit. The private charter on the Bright Star II which Brian Captains was unforgettable and a very special treat for our anniversary. If you seek a lovely cottage with easy access to water and your own private retreat, this cottage is the place to visit. Plus Bermuda is one of the most beautiful places on earth- fantastic visit. Thank you.

  • Review Submitted: Aug 10, 2015
  • Date of Stay: Jul 2015
  • Source: VRBO, from HomeAway
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Esquimalt, BC

Comfort and Joy

  • 5 of 5

We had a delightful two week stay at Oyster Point...all the comforts of home...easy to get to by taxi from the airport, ( approx $40 - not expensive) and Dorothy was kind enough to sock in the essentials into the fridge for our arrival. The cottage is perfectly situated, lovely crossbreezes, shaded patio, sunset views every night...a stroll down to a private beach on the bay. Walk back up the road and up and over the hill to the grocery store (be careful as the sidewalks are narrow) Catch the bus anywhere on the island, so easy and everyone is so unerringly polite and helpful. Caught the courtesy bus from the Fairmont Southhampton up to the hotel, and then down to Horseshoe Bay beach on the south shore ..perfection....We highly recommend going to Harbour Nights in Hamilton, and to the Beluga Bar for sushi...best ever. The cottage has such a delightful comfy bed...comfy couches...all the towels and supplies you could possibly need. We did not need the airconditioning at all. The cottage could use a bit of a deeper cleaning in places but all was well. Brian and his daughter hosted us on a sail on the Bright Star...fantastic tour and food ...an unforeseen mechanical problem resulted in no actual sailing...but still a fantastic day on the water...Abby and Zoe delightful...thanks for the great holiday! Bermuda is truly comfort and joy

  • Review Submitted: Jun 30, 2015
  • Date of Stay: May 2015
  • Source: VRBO, from HomeAway
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Scottsdale, AZ

As described - but it was not a good visit

  • 3 of 5

We were delayed one day getting in because of tropical storm Fay and then the second day we didn't arrive until nearly midnight. Dorothy and Brian were there to greet us as were the previous guests who could not get out. They were gracious and warm. They did not charge us for the day we could not get onto the island.

The next morning we awoke to a wonderful day, but the grounds of Oyster Point were a mess and many amenities were unavailable or broken due to debris and on Bermuda with an island to cleanup, nothing was going to improve at Oyster Point for several weeks.

Immediately we were informed via the weather reports that a second real hurricane (Gonzalo) was approaching, and that we really should try to get off of the island as a storm that big can take out the airport causeway for weeks. Of course, this was everyone's idea as well and flights were nearly impossible - and with a PGA event going on to increase the pressure. We eventually found a very expensive way off of the island - and had a verbal agreement from Brian that he and I would split the cost of the unused days at Oyster Point 50/50 and that this would be forthcoming upon our leaving. Upon departure, there was no refund - he told me that he didn't have any American money - "I will take Bermudian dollars (one for one exchange) - No", "You can write me a check - No". was his response. He offered me a possible discount should we decide to come back some day. I got into my expensive cab and drove away. My wife and my 25th anniversary was an unfortunate and very expensive event.

I have thought long about this review and I want to be clear, Oyster Point is beautiful and if things had gone as planned I am certain we would have had a terrific time. I also understand the weather is not controllable by our hosts. My only real complaint is when our agreement to split the loss - caused by the weather wasn't honored due to an excuse of "I have no American money". We wont go back to Bermuda. For our money Hawaii is much more beautiful and not directly in the storm belt. For the two days we were there, between storms - we did have a good time.

  • Review Submitted: Jun 17, 2015
  • Date of Stay: Oct 2014
  • Source: VRBO, from HomeAway
Owner's Response: It has been 8 months since these guests came to stay at our cottage for 4 nights which unfortunately was between Hurricane Fay and Hurricane Gonzalo which both passed over Bermuda. We welcomed these guests upon their late arrival with drinks and nibbles at our home next door and later they settled into the cottage. Admittedly, we did have foliage debris on the lawn in front of our home from Hurricane Fay, which had just hit the Island a couple of days before, but the cottage grounds had been cleared and cleaned for the arrival of our guests. There was nothing broken and the cottage was fully functional with electricity and all the comforts of home. Our guests were scheduled to move from our cottage to the Fairmont Southampton Princess Hotel the morning of the 17th October for several days of a conference, which as it happens was cancelled after they arrived on the island. If their return flights had been scheduled for the end of their stay with us there would have been no problem leaving the Island before the arrival of Hurricane Gonzalo as our airport was open for incoming and outgoing flights at this time. We therefore felt it was their choice to leave our cottage 2 days early because of the cancelled conference. As mentioned in this unfortunate, unfair and negative review we did not charge for the first day of their reservation and have offered a couple of days discount on a future visit to Bermuda and our cottage. We hope they will reconsider a return trip to Bermuda where we can offer our hospitality again and see the “Bermudaful” and welcoming island, under normal circumstances, that Bermuda is so famously regarded as.
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Enter as strangers, leave as friends

  • 5 of 5

Everything that people have written about Oyster Point is true: Breathtaking and idyllic location, close to restaurants, beaches, and a marketplace, a private and fully stocked cottage filled with essentials.

Although necessary and important, these components are not what make Oyster Point remarkable. The element that makes Oyster Point so special is our Hosts: Dorothy, Brian, their family and of course, Abbie and Zooey. My husband and I had an unplanned extension to our vacation, as tropical storm Fay hit the island. Brian and Dorothy couldn't have been more accommodating to us. We were treated like family friends. I'm still a bit stunned how warm, kind and welcoming they were to us.

You may notice when staying at Oyster Point the framed print on the wall stating: 'Enter as strangers, leave as friends'. Perhaps that saying may be trite elsewhere, but at Oyster Point, the statement is fact. Thank you, we will be back!

  • Review Submitted: Oct 17, 2014
  • Date of Stay: Oct 2014
  • Source: HomeAway
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Prices & Availability

Prices for this holiday cottage in Bermuda, North America

Rental Basis:
per property
Owner accepts payment in:
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Rental Period Minimum Price Additional Nights Weekend Night Weekly Monthly Event Price
My Standard Rate
3 night minimum stay
for 3 nights
Notes: Rates are based on 2 guests; add £34 per night, per additional guest
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Available arrival
Calendar not updated in over 2 months and may not be available. Look for rentals with Request to Book or updated calendars.


Accommodation and facilities for this holiday cottage in Bermuda in North America

Property Type:
  • cottage
  • Self-catering
Location Type:
  • Beachfront ...
  • Water View ...
  • Waterfront ...
  • Away From It All
  • Romantic
  • Air Conditioning
  • Hair Dryer
  • Heating
  • Iron & Board
  • Linens Provided
  • Living Room
  • Telephone ...
  • Towels Provided
  • Wireless Internet
  • Wood Fireplace
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Ice Maker
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator
  • Hob
  • Toaster
  • Child's Highchair
  • Dining Area
  • 1 Bathroom
  • Bathroom 1 -
  • 1 Bedroom, Sleeps 4
  • Bedroom 1 - 1 Large Double Bed
    rollaway beds - 1 Single Bed , 1 Cot , 1 Sofa bed/Futon , single sleep sofa, one rollaway bed and crib
  • Queen size Beds (1), Baby Cribs (1) rollaway beds (1) small sleep sofa (1)
  • Books
  • CD Player
  • DVD Player
  • Games
  • Satellite / Cable
  • Stereo
  • Television
  • Terrace ...
  • Gazebo ...
  • Kayak / Canoe
  • Garden
  • Barbecue
  • Water Sports Gear
  • children welcome ...
  • non smoking only ...
  • pets not allowed
  • wheelchair accessible ...
Pool / Spa:
  • Hot Tub
  • Sauna
  • botanical garden
  • cinemas
  • Health/Beauty Spa
  • library
  • museums
  • restaurants
Leisure Activities:
  • beachcombing
  • Boating
  • horse riding
  • Miniature golf
  • scenic drives
  • Shopping
  • sight seeing
  • walking
  • whale watching
  • Wildlife Viewing
Local Services & Businesses:
  • ATM/bank
  • fitness centre
  • groceries
  • hospital
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • hiking
  • jet skiing
  • Kayaking
  • Parasailing
  • sailing
  • snorkelling
  • Snorkeling/Diving
  • surfing
  • swimming
  • tennis
  • wind-surfing
Small private beach, kayak, snorkeling equipment, close to public beaches, bus stops, grocery store, restaurants, The Fairmont Southampton Princess Hotel with spa, tennis, golf facilities etc., hiking trails, Gibbs Hill Lighthouse and other interesting places to visit..

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Portable wifi hotspot

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