Samish Island Luxury Vacations 2026

Photo by Theresa McLaird

Top Luxury vacation packages in Samish Island

Price found within the past 48 hours. Click for updated prices.

The Wild Iris Inn

$557

per person

Oct 9 - Oct 11

found 1 day ago

Roundtrip flight included

San Luis Obispo (SBP) to Bellingham (BLI)

9.4/10 Exceptional! (875 reviews)

Gorgeous property with finely decorated rooms, upgraded amenities like a private jacuzzi tub on a private back deck, and delicious breakfast!

Reviewed on Sep 2, 2026

Otters Pond Bed & Breakfast

$580

per person

Oct 9 - Oct 11

found 1 day ago

Roundtrip flight included

San Luis Obispo (SBP) to Eastsound (ESD)

10/10 Exceptional! (70 reviews)

Amazing!

Reviewed on Aug 29, 2026

Chrysalis Inn & Spa Bellingham, Curio Collection by Hilton

South Hill

$865

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip flight included

San Luis Obispo (SBP) to Bellingham (BLI)

9.2/10 Wonderful! (950 reviews)

Morning Glory by Avantstay Lower-level Whidbey Hideaway Water Views + Shared Hot Tub

$911

per person

Oct 10 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Bellingham (BLI)

No reviews

Don't see what you're looking for?

See all available trips from Columbus to Samish Island

View all trips

3 Night Luxury vacations in Samish Island

Price found within the past 48 hours. Click for updated prices.

The Wild Iris Inn

$659

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip flight included

San Luis Obispo (SBP) to Bellingham (BLI)

9.4/10 Exceptional! (875 reviews)

Gorgeous property with finely decorated rooms, upgraded amenities like a private jacuzzi tub on a private back deck, and delicious breakfast!

Reviewed on Sep 2, 2026

Chrysalis Inn & Spa Bellingham, Curio Collection by Hilton

South Hill

$865

per person

Oct 8 - Oct 11

found 1 day ago

Roundtrip flight included

San Luis Obispo (SBP) to Bellingham (BLI)

9.2/10 Wonderful! (950 reviews)

Morning Glory by Avantstay Lower-level Whidbey Hideaway Water Views + Shared Hot Tub

$911

per person

Oct 10 - Oct 13

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Bellingham (BLI)

No reviews

Don't see what you're looking for?

See all available trips from Columbus to Samish Island

View all trips

4 Night Luxury vacations in Samish Island

Price found within the past 48 hours. Click for updated prices.

Raintree's Sandcastle

$488

per person

Oct 5 - Oct 9

found 1 day ago

Roundtrip flight included

Oakland (OAK) to Bellingham (BLI)

9.4/10 Exceptional! (683 reviews)

The Resort is really nice, very clean. Furnishings are a bit dated but they do have a beachy theme. Resort is across the street from the beach. Walking trails behind the Resort. Great views of Sunsets. Bars and restaurants close by. Staff is friendly and accomodating.

Reviewed on Sep 3, 2026

Inn to the Woods B&B

Save 100% on your flight

$698

per person

Oct 5 - Oct 9

found 1 day ago

Roundtrip flight included

Oakland (OAK) to Friday Harbor (FBS)

9.8/10 Exceptional! (106 reviews)

It was such a cute place. My husband and I enjoyed our stay there. It is tucked in the woods as the name suggests. The breakfast was very good. We had gluten free lemon blueberry pancakes and they were delicious.

Reviewed on Aug 26, 2026

Lodge at Deception Pass by Avantstay Trails, Hot Tub, Walk to Cornet Bay

Save 100% on your flight

$1,321

per person

Oct 5 - Oct 9

found 1 day ago

Roundtrip flight included

Oakland (OAK) to Bellingham (BLI)

No reviews

Don't see what you're looking for?

See all available trips from Columbus to Samish Island

View all trips

What can I expect from a luxury Samish Island vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Samish Island vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Samish Island?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Samish Island luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $488. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Samish Island?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Samish Island with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Samish Island?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Samish Island with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Samish Island with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.