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

'The Homestead' on Eastsound's Waterfront!

Bedrooms 4
Space 2,200 sq ft
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
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks: english, spanish
Response time:
Within an hour
Response rate:
Calendar last updated:
September 21, 2018

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 Eastsound

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:
  • Check-in: 4:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 11
  • Children welcome
  • Parties/events not allowed ...
  • Pets considered ...
  • Non smoking only
  • Please be courteous of neighbors. No noise after 9 p.m. or before 8 a.m.
  • All furniture, including outdoor seating, must be returned to its original location.
  • Prior to departure please strip beds, run dishwasher, and tidy up.
Location Type:
  • Ocean View ...
  • Oceanfront ...
  • Water View
  • Adventure
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Broadband Access
  • Clothes Dryer
  • Elevator
  • Fireplace
  • Gas Fireplace ...
  • Hair Dryer
  • Heating
  • Internet
  • 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 -
(78 traveler reviews)

96% Complete
2% Complete
1% Complete
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'The Homestead' on Eastsound's Waterfront!
average rating of 4.948718 based on 79 reviews

ideal Orcas vacation home

  • 5 of 5

A beautiful and homey house, highly functional outdoor space, a picturesque landscape, and an ideal location right next to Eastsound... it doesn't get better than this house!

  • Submitted: Aug 25, 2018
  • Stayed: August 2018
  • Source: VRBO, from HomeAway
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We were at the Homestead for two nights. 8 of us didn’t want to leave. A great venue. Very clean.

  • 5 of 5

We drew for rooms. Everyone liked what they drew. Even the bunk bed couple. Eastsound is small so we walked all over town. We had a great breakfast at the Skillet. The house is well maintained and very clean. My friends kept thanking me for finding the Homestead.

  • Submitted: Aug 25, 2018
  • Stayed: August 2018
  • Source: VRBO, from HomeAway
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Seattle, Washington

Weekend at The Homestead

  • 5 of 5

The Homestead was the perfect place for gathering our extended family to celebrate my wife's 70th birthday. The sleeping accommodations were ample and comfortable for the ten of us (plus an infant). The kitchen was well equipped and didn't lack anything essential. The utensils were of good quality, not the usual Ikea stuff. The location is great, only a short walk from the downtown area of Eastsound, and the view of the water was beautiful and restful. We would stay gain at The Homestead in a heartbeat.

  • Submitted: Aug 14, 2018
  • Stayed: August 2018
  • Source: HomeAway
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South Carolina

Every detail addressed

  • 5 of 5

Susan responded immediately to every question and the place is unbelievable. It carries an aura of history while being up to date in every way. One of our favorite places! Location is ideal and views breathtaking.

  • Submitted: Aug 6, 2018
  • Stayed: August 2018
  • Source: VRBO, from HomeAway
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Perfect Spot

  • 5 of 5

Perfect location, beautifully appointed. Rare to stay in a property where you even like the serving dishes.

  • Submitted: Jul 28, 2018
  • Stayed: July 2018
  • Source: VRBO, from HomeAway
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  • 5 of 5

We enjoyed staying here very much. Perfect for our family reunion. It is right in town but also feels peaceful at night with a lovely view of the water.

  • Submitted: Jul 6, 2018
  • Stayed: June 2018
  • Source: VRBO, from HomeAway
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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.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $150
Pet Fee $40

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

  • 50% refund if canceled at least 14 days before arrival date.
  • 100% refund if canceled at least 30 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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