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'The Homestead' on Eastsound's Waterfront!

Bedrooms 4
Property type house
Minimum Stay 2 nights


About the property

House, 4 Bedrooms + Convertible bed(s), 2 Baths, (Sleeps 8-10)

Enjoy your vacation in this delightful, lovingly renovated vintage island home! Built by settlers in 1908, it embodies the fascinating history of these beautiful San Juan Islands. The house is centrally located in Orcas Island's Eastsound Village -- called one of the most charming travel destinations in America. Partially fenced yard with lovely landscaping ensures your privacy, while enjoying proximity to all conveniences. This coastal classic is equally appealing for a romantic get-away, or for a gathering of family and friends.

Stroll to Orcas Island's Farmer's Market and barbeque on your deck, or enjoy a meal in one of Eastsound's heralded restaurants offering world-class cuisine. A bookstore and lattes are just around the corner, and whalewatch tours and/or kayak rentals can be arranged nearby. Walk to the public dock just yards away for boating excursions. Watch sunsets, eagles, and the abundant wildlife around Indian Island. Facing southwest, your view includes the bay, shoreline of picturesque Eastsound, and unmatched island sunsets. Only seven miles from the ferry landing, four miles from Turtleback Mountain Preserve, and five miles from majestic Moran State Park and Mt. Constitution, this location is really the perfect hub for your trip.

Four bedrooms offer lots of privacy, with one bedroom on the ground floor and three upstairs. Master bedroom overlooks the gorgeous view. Fully equipped kitchen with all amenities. Large flatscreen TV's in the living room and downstairs bedroom with Directv satellite service and DVD players. Enjoy a drink on the deck and lounge on the roomy stone patio with its beautiful propane fire pit. Absorb the magic of Orcas Island. We look forward to welcoming you!

(Well-behaved pets welcome).

If the Homestead is booked for your desired dates, please check out our delightful NEW listing on VRBO, #702366.

Keywords: Historic, completely restored

More Details

Susan Gudgell
Member since: 2011
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
March 21, 2017

About Susan Gudgell

We have been on Orcas Island for many decades (in fact Wally grew up here!) so are true islanders. We can suggest not only major travel activites, but little known gems on island backroads. We are raising two daughters here -- no better place in the world!

Susan Gudgell purchased this house in 2006

Why Susan Gudgell chose Orcas Island

We have always loved this house as it is an intrinsic architectural element on the charming Eastsound shoreline. We welcomed the opportunity to restore it to its original glory.

What makes this house unique

Sipping coffee or a glass of wine on the deck, breathing in that clear island air, and contemplating the view! We also love wandering around the village, hiking in the Turtleback Mountain Reserve, and exploring Moran State Park. We know many of the restauranteurs in town and love the many delicious varied options for an evening out.

Guestbook comments from the owner

Thank you for helping make our first trip to Orcas Island such a pleasant one. The Homestead was a great place to relax and unwind, and the location was perfect for exploring the rest of Orcas. Thanks again and hope to be back in the future!
Mar 2013
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Eastsound House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 2200 sq. ft.
House Rules:
  • Max. occupancy 11
  • non smoking only
  • pets considered
  • Events Allowed
  • children welcome
Location Type:
  • Ocean View ...
  • Oceanfront ...
  • Water View
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Broadband Access
  • Clothes Dryer
  • Gas Fireplace ...
  • Hair Dryer
  • Heating
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking ...
  • Parking Off Street
  • Parking for RV/Boat/Trailer
  • Telephone ...
  • Towels Provided
  • Washing Machine
  • Wireless Internet
  • Catering Available ...
  • Coffee Maker ...
  • Cooking Utensils
  • Dishes & Utensils ...
  • Dishwasher
  • Ice Maker
  • Kitchen ...
  • Microwave
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 10 people
  • 2 Bathrooms
  • Bathroom 1 - toilet , combination tub/shower , jetted tub , Large clawfoot tub
    Bathroom 2 - toilet , combination tub/shower , Small clawfoot tub
  • 4 Bedrooms, Sleeps 11
  • Bedroom 1 - 1 queen
    Bedroom 2 - 1 queen
    Bedroom 3 - 1 double
    Bedroom 4 - 2 bunk bed , 4 twin beds total
    Bedroom 5 - 1 twin/ single , daybed on the upstairs landing.
  • Queen size Beds (2), Double Beds (1), Twin or Single Beds (4), Daybed (1)
  • Books
  • CD Player
  • DVD Player
  • Games
  • Satellite / Cable
  • Stereo ...
  • Television
  • Toys ...
  • VCR
  • Video Library
  • Deck / Patio ...
  • Golf ...
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Outdoor Grill
  • 8 garden chairs
  • limited accessibility
Pool / Spa:
  • jetted tub
Onsite Services:
  • Concierge
  • Massage
  • churches
  • cinemas
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
  • winery tours
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • horseback riding
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • fly fishing
  • freshwater fishing
  • golf
  • hiking
  • kayaking
  • racquetball
  • sailing
  • scuba diving or snorkeling
  • sound/bay fishing
  • swimming
  • tennis


Wonderful! 4.9/5 -
(58 traveler reviews)

'The Homestead' on Eastsound's Waterfront!
average rating of 4.948276 based on 59 reviews

A friendly getaway

  • 5 of 5

My friends and I stayed at the Homestead for a weekend on Orcas Island, and I found the house to be comfortable for all of us. Not only is the property gorgeous and the home spacious and relaxing, but there were plenty of towels, dishes, glassware and space for 8 people to constantly be in and around the kitchen on a mission to find food. I would stay at this house again in a heartbeat - or perhaps never leave.

  • Submitted: Jan 30, 2017
  • Stayed: Jan 2017
  • Source: VRBO, from HomeAway
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Perfect spot on Orcas Island

  • 5 of 5

We just returned from a great week at "The Homestead" on Orcas Island. While we had read the outstanding reviews of the property - we were still surprised by the perfect location and cozy house. We were on Orcas for my son's wedding in Eastsound and seven of us were very comfortable using The Homestead as our base. We parked the car when we arrived, and since restaurants, shops and the grocery store were all within a few blocks, we did not need our car for our stay. The house is decorated in a "cottage look" with all the supplies you might need for a week-long stay on the island. There was a BBQ on the large deck, plenty of plates, glasses (for toasting the happy couple) and even a stackable washer and dryer. The view of the water from the kitchen and deck was incredible - and the gas fire pit out back was a great way to connect with our group in the evening. We highly recommend The Homestead for a peaceful vacation.

  • Submitted: Oct 1, 2016
  • Stayed: Sep 2016
  • Source: VRBO, from HomeAway
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Petaluma, CA

Utterly fantastic VRBO - perfect in every way!!!

  • 5 of 5

My family gathered at the Homestead to celebrate our son's wedding. The home was beautifully set up with comfy mattresses, lovely linens, and tons of fluffy white towels. The kitchen had everything we needed to host a rehearsal dinner for 45 outside on the stunning stone patio (including 15 platters!)(We rented 2 tables for 8 but there were enough other tables on site to accommodate everyone else). The view of the bay is lovely, and we had dinner overlooking the water, enjoying the sunset. Susan, the owner, gave me her personal cell phone so I could check in with her. I called three times with questions (garbage, a glass I broke, etc.) and each time she picked up immediately and helped me with my question. She even welcomed us in person when we arrived. All my guests were wowed and several want to rent the house themselves for a future vacation on lovely Orcas. An added bonus is that the house is on a quiet street but right next to Eastbound - a village with everything from a supermarket (100 yards away) to fantastic bakeries, restaurants, ice cream shops, and kayak rentals.

  • Submitted: Aug 17, 2016
  • Stayed: Aug 2016
  • Source: VRBO, from HomeAway
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We celebrated our 50th anniversary with family at The Homestead. It was a wonderful stay

  • 5 of 5

The Homestead is a wonderful facility and is equiped as described. The vee is very nice. The house is spacious and accompanied the 8 adults in our group very well. The kitchen is well supplied with most everything the gourmet co would require. It is an easy five-minute walk to the center of Eastsound Village and a very nice full-service grocery store with bakery and deli. The only thing that might give some persons with physical limitations pause is the showers are in claw-footed tubs with quite high sides. They worked for us but might be a challenge for some. We loved our stay (July 27-August 3) and heartily endorse The Homestead as a fine place to stay on Orcas Island.

  • Submitted: Aug 4, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
Owner's Response: We loved hosting your family for such a special event and are very glad you enjoyed it! Just so future guests are aware, we do have a special, medically designed shower stool at the house to assist guests with tub access should they have mobility challenges. Thanks again and we hope you'll come visit us in the future.
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We just booked our third visit -- need I say more?

  • 5 of 5

It is difficult to imagine a better location from which to enjoy a family vacation on Orcas Island. And, the owner is a delight to deal with. While you are at this house, you will find yourself drawn outside to the upper deck seating area, or the larger slate patio below, to relax and enjoy a truly spectacular view of East Sound and Indian Island. The fresh seafood in this area is one of the main attractions for us, and this house is perfect for a family or group that wants to cook and enjoy meals together. Tables and benches on the patio allow a large group to dine outside and enjoy the view. Inside, the kitchen/dining area is also great for group meals and entertaining. The house is clean and comfortable. If you are interested in meandering through the shops, galleries, restaurants and other attractions of charming Eastsound Village, you need only walk out the front door and around the corner. If being out on the water is your thing, a public dock within walking distance at the end of the street provides a convenient put-in point for kayakers. Five minutes to the North is a private marina offering short-term moorage as well as a variety of charter services. If you visit this property, you will probably want to do what we did -- book next year's stay before you leave.

  • Submitted: Jul 20, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
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Very nice and great location for the town.

  • 4 of 5

This was just the right place for our family coming from all over the country for a wedding. House size was great and location was very relaxing for all of us with being on top of each other. The house layout worked well for us and the beauty of the view was so nice!

  • Submitted: Jun 23, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
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Rates & Availability

Eastsound House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Quiet Season 2016-2017
Oct 1 2016 - May 31 2017
2 night minimum stay
Summer 2017
Jun 1 2017 - Sep 30 2017
2 night minimum stay
Quiet Season 2017-2018
Oct 1 2017 - May 31 2018
2 night minimum stay
My Standard Rate
2 night minimum stay

Additional information about rental rates

Pet Fee $40 + Tax
Cleaning Fee $75 + Tax
Tax Rate 10.1%

Deposit is refundable up to 30 days prior to scheduled arrival, less $40 booking fee. Shorter stays possible with additional cleaning fee. Longer term stays possible at reduced price to be negotiated with owner.

Owner's Cancellation Policy

100% refund if canceled at least 30 days before arrival date.
Enter dates for accurate pricing
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Nearest Airport
0.75 Miles
Eastsound Airport
Nearest Barpub
Madrona Bar & Grill, Lower Tavern
Nearest Ferry
6 Miles
Orcas Landing
Nearest Golf
1.5 Miles
Orcas island Country Golf Course
Nearest Restaurant
The Loft at Madrona
Nearest Beach
Fishing Bay
Car: not necessary

Whalewatching, wildlife tours, the Orcas Cultural Center offers fabulous music performances and theatrical productions.


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