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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Luxury Home - Quintessential Maine and Classic Kennebunkport! Now booking 2018

Bedrooms 5
Half Baths1
Property type house
Minimum Stay 7 nights


About the property

Perfect 1889 Shingle Cottage (5 Beds, 2.5 Baths) In A Historic Neighborhood

New for 2018:-

- Our new gym is up and running, it is well equipped including a range or weight and cardio exercise options

- Our new outdoor shower enclosure, allowing you to fully enjoy a shower al fresco, either coming back from the beach or just because

- We have extended our landscaping to include a large further pacel of land at the back of the house, provide plenty of additional room for relaxing

- The master bathroom has been newly retiled

- The house has a fresh coat of paint throughout

Quintessential Maine and Classic Kennebunkport! 'Shady Oak' is a 1889 shingle cottage located in the historic Cape Arundel neighborhood (listed on the National Register of Historic Places) of Kennebunkport - one block from the ocean, a 5 minute walk to the Colony Beach (a great beach for kids) and a short walk to the Port, with its many shops, galleries and restaurants. This idyllic Victorian house is located just around the corner from St Ann's Church, the Kennebunk River Club and Walker’s Point (summer home of President George H.W. Bush).

The house boasts 5 bedrooms, including a master suite (ground floor), and 2 1/2 baths (plus an outdoor shower!). The bedroom configuration is California king (master), 1 queen, 2 twins, bunk room (bunk bed, single over double with a single trundle) and queen pull-out sofa. In addition to a fully equipped kitchen, there is a dining room, family room and sitting room.

You can also enjoy the screened in porch, an outside patio / living room and an outside dining room under a custom made pergola. The stunning professional landscaping creates a wonderful environment with extensive stone walls and plantings designed to be at their peak in June, July and August.

Other amenities include:

• Full gym

• Nespresso coffee maker

• Hi-speed Wifi

• 2 TVs

• 2 DVD players and 100s of DVD

• Wii

• Apple TV

• Netflix


• Fire Pit (with lots of wood)

• Large gas BBQ grill

• Washer and Dryer

• Dishwasher

• Loads of board and other games and puzzles

• lots of books

More Details

Michael and Anne Dakin
Member since: 2013
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
February 20, 2018

About Michael and Anne Dakin

Anne and Michael were married at St Ann's in Kennebunkport, just steps away from Shady Oak. Anne and Michael have a deep love of Maine, Anne spent summers with her grandparents in Cape Porpoise and Kennebunkport while Michael's family have long history Down East.

Michael and Anne Dakin purchased this house in 2007

Why Michael and Anne Dakin chose Kennebunkport

Shady Oak is an oasis, enjoy the ultimate relaxation in a beautiful environment. The house itself is very special and harkens back to the history of Kennebunkport as a resort community. Steps away from the ocean and minutes from town, this is the perfect location to enjoy everything the Maine coast has to offer, or do nothing at all but kick-back and enjoy yourself.

What makes this house unique

Historical house and location with all the amenities you would want. Beautiful gardens and ample space make this the perfect vacation getaway.


Kennebunkport House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Included
House Rules:
  • Max. occupancy: 10
  • children welcome
  • pets not allowed
  • non smoking only
Location Type:
  • Ocean View ...
  • Village ...
  • Water View ...
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Clothes Dryer
  • Fireplace ...
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Living Room
  • Parking
  • Telephone
  • Washing Machine
  • Coffee Maker ...
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Pantry Items
  • Refrigerator
  • Stove
  • Toaster
  • Dining ...
  • Dining Room
  • seating for 10 people
  • 2 Bathrooms
  • 1 Half Bath
  • Bathroom 1 - toilet , shower , jetted tub
    Bathroom 2 - toilet , shower
    Bathroom 3 - toilet
    Bathroom 4 - shower
  • (1) Master ensuite bathroom with tub and shower (2) Upstairs bathroom with toilet and shower (3) Downstairs cloakroom with toilet (4) Outdoor shower
  • 5 Bedrooms, Sleeps 10
  • Bedroom 2 - 1 queen
    Bedroom 3 - 2 double
    Bedroom 4 - 1 double , 2 twin/ single , Bunk Room
    Bedroom 5 - 1 sleep sofa /futon , Queen size pull-out sofa and TV/DVD player
    Bedroom 1 - 1 king , Master with ensuite, also has a chaise lounge (ground floor)
  • 5 bedrooms - (1) Master bedroom - California king bed, en suite bathroom with jacuzzi tube and shower (ground floor) (2) 2nd Bedroom - Queen size bed (3) 3rd Bedroom - two (2) twin beds (4) Bunkroom - single bunk over a full size bed with a single trundle (5) 5th Bedroom / Den - queen size pull out sofa (with TV and DVD player)
  • Books
  • DVD Player
  • Games ...
  • Satellite / Cable
  • Stereo
  • Television ...
  • Toys
  • Video Games
  • Video Library ...
  • Deck / Patio
  • Golf ...
  • Lanai / Gazebo ...
  • Lawn / Garden ...
  • Outdoor Grill
  • Tennis ...
  • Water Sports Gear ...
  • wheelchair inaccessible
Onsite Services:
  • Concierge
  • autumn foliage
  • churches
  • coin laundry
  • festivals
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • horseback riding
  • outlet shopping
  • photography
  • scenic drives
  • sight seeing
  • walking
  • whale watching
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • hiking
  • sailing
  • surfing
  • swimming
  • tennis


Exceptional! 5/5 -
(16 traveler reviews)

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Luxury Home - Quintessential Maine and Classic Kennebunkport! Now booking 2018
average rating of 5.0 based on 16 reviews

Beautiful home - perfect for a family vacation!

  • 5 of 5

We had an amazing experience with this rental property. The team (owners, property manager, and cleaning services) all worked seamlessly with the objective of making our stay as enjoyable as possible. The deck was an amazing feature - we had dinner on the deck three nights! Kitchen was well sized and worked great for us, and bedrooms were perfect. We comfortably had 10 people, including young kids, in the house, and there was a space for everyone! Amazing experience, and highly recommend this property!

  • Submitted: Oct 24, 2017
  • Stayed: August 2017
  • Source: HomeAway
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The Best of Kennebunkport

  • 5 of 5

We rented in 2016 and loved it so much we returned in 2017. The house is as lovely as it is in the photos and the landscaping is gorgeous. Upon our arrival, the property manager was very helpful and told us we could call him with any questions. The location is ideal as we could walk to many places including the Colony Beach, St. Ann's and Mabel's Lobster Claw, which is a fun place to go for an ice-cream cone. Loved having morning coffee on the front porch. Afternoons and evenings were spent on the back patio and at the table under the pergola. Making s'mores over the fire pit was always a fun activity after dinner. There is a nice table inside which is perfect for doing jigsaw puzzles. We played a bit of golf at Cape Arundel, a beautiful semi/private golf course a few miles away. We also rented kayaks in Dock Square and kayaked on the Kennebunk River and also in Cape Porpoise. Portland is about 40 minutes north so for a change of pace one day we went up to the Portland Museum of Art. This past summer we also saw a play at the Ogunquit Playhouse (about 30 minutes south) and a comedian at Vinegar Hill which is a wonderful venue a few miles away. There is so much to do in this charming little town and Shady Oak is the perfect place to stay.

  • Submitted: Oct 16, 2017
  • Stayed: June 2017
  • Source: HomeAway
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It was a wonderful experience

  • 5 of 5

We really enjoyed our stay and especially the outdoor entertaining areas. There were seven of us and even on rainy days we were comfortable. Great home and location.

  • Submitted: Oct 16, 2017
  • Stayed: August 2017
  • Source: HomeAway
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Cape Arundel Beauty!

  • 5 of 5

Shady Oak

Wow! The reviews of Shady Oak are spot on. It is a beautiful, historic home that exudes comfort and tranquility. The gardens and hardscape could be in a Home and Garden magazine... blooming hydrangea, lavender, roses and a gorgeous stone firepit that kept us warm and enchanted on several chilly October nights.

The kitchen truly had everything you could possibly need to make an exceptional meal...which we did! The bedrooms were understated and simply decorated and the master bedroom had the most comfortable bed we’ve slept on in years... We’re buying one when we get home!

The location could not be any better - right in the heart of Cape Arundel near Walker’s Point and a short walk to the rocky coastline and Cape Arundel Inn for cocktails on their porch - one of our favorite things to do.

The owners and Caretaker, Steve were so attentive and helpful during our stay. We felt so welcome and tended to. My husband and I can’t say enough about this home and it’s owners... we won’t soon forget this much needed respite and can’t thank them enough for allowing us into their cherished home.

  • Submitted: Oct 15, 2017
  • Stayed: October 2017
  • Source: HomeAway
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  • 5 of 5

I loved this home! It was my families first visit to Maine and this was the perfect size for all 9 of us adults to spread out. Indoor and outdoor dining areas were the perfect size for meals and game nights. I even brought my 20 month old and he did well. House was basically toddler friendly except for a few minor things I had to place at a higher level. The house was quiet at this time of year and a great walk to the beautiful water and rocky coastline. It was about a mile walk to the downtown area that several of my family members enjoyed. House had everything we needed for our week visit!

  • Submitted: Jul 5, 2016
  • Stayed: May 2016
  • Source: HomeAway
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Lovely throughout

  • 5 of 5

The Dakins' home exceeded our expectations. Perfect location is walking distance to Colony Beach and town of Kennebunkport. The property manager, Steve, welcomed us and was a font of information. The house is beautiful, comfortably decorated, and has a screened-in front porch (our 8-month old granddaughter loved the baby-sized Adirondack chair!), back patio, lush landscaping, huge outdoor grill and eating area. We didn't get a chance to use the firepit. House was just the right size for our 9-person family. Beds are super comfortable. The kitchen was fully stocked with most staples so we did not have to buy much. Washer and dryer in laundry room are better than the ones I have at home. Only negative mentioned by our adult kids was they wish there was a second bathroom upstairs, but they came down and used ours sometimes so it really was not an issue. i was worried about the lack of air-conditioning but we did not need it in June with the windows open and several fans in the home.

It is obvious that this home is cherished by its owners as well as used by them. We thoroughly enjoyed our week at Shady Oak and will definitely be back.

  • Submitted: Jun 25, 2016
  • Stayed: June 2016
  • Source: VRBO, from HomeAway
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Nearest Airport
25 Miles
Portland International Jetport (Portland, MW)
Nearest Barpub
0.3 Miles
The Colony Hotel / Stripers @ The Breakwater
Nearest Golf
2.5 Miles
Cape Arundel Golf Club
Nearest Train
9 Miles
Wells, ME
Nearest Motorway
7 Miles
Nearest Restaurant
0.3 Miles
The Colony Hotel / Stripers @ The Breakwater
Nearest Beach
0.4 Miles
Colony Beach
Car: recommended

St Ann's Church and the Kennebunk River Club are just a short walk from the house, perfect if you are attending an event at one of these venues. In addition, Dock Square (the center of town or 'the Port'), featuring numerous shops and restaurants, is a short walk or bike ride away.

You can walk to a number of restaurants, as well as a spa and other amenities. If you love lobster, the lobster pound (Port Lobster) is just minutes away; order your lobsters in advance and pick them up already cooked, all you need to do is bring them back to the house and enjoy them, perhaps outside under the custom and iconic pergola.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Property Damage Protection $59
Refundable damage deposit $500
Cleaning Fee $250
Tax Rate 9.0%

Check-ins are generally scheduled for Saturday afternoons such that stays run from Saturday to Saturday, but please do contact us if you are interested in alternate days.

Please note that we are willing to allow events to be held at the house but only with our prior consent and subject to agreed terms.

Please note that pursuant to Maine law we are required to charge 8% sales tax on rentals.

Owner's Cancellation Policy

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

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