A coastal cityscape with a vibrant sunset sky, dense urban area, and distant mountains.

Winchester Vacation Packages

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The Latest Winchester Vacation Packages

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

Jan 18 - Jan 22
Drift Santa Barbara, a Member of Design Hotels + Flight
Downtown Santa Barbara
4 nights
3.5 star property
8.4/10 - Very good (508 reviews)
Roundtrip • Kamloops (YKA) - Santa Barbara (SBA)
YKA - SBA • 2 stops SBA - YKA • 2 stops
~~CA $2,296~~
CA $1,936
per traveller
found 2 hours ago
Drift Santa Barbara, a Member of Design Hotels
Jan 18 - Jan 22
El Encanto Santa Barbara + Flight
Upper Riviera
4 nights
5.0 star property
9.4/10 - Exceptional (618 reviews)
"Spend two nights here for our wedding and it was perfect! Such a special place!"
Reviewed November 6, 2026
Roundtrip • Kamloops (YKA) - Santa Barbara (SBA)
YKA - SBA • 2 stops SBA - YKA • 2 stops
~~CA $3,920~~
CA $3,080
per traveller
found 2 hours ago
El Encanto Santa Barbara
Jan 18 - Jan 22
Brisas del Mar, Inn at the Beach + Flight
Santa Barbara Beach
4 nights
3.5 star property
9.4/10 - Exceptional (1,462 reviews)
"The staff was very welcoming. Nice amenities."
Reviewed November 4, 2026
Roundtrip • Kamloops (YKA) - Santa Barbara (SBA)
YKA - SBA • 2 stops SBA - YKA • 2 stops
~~CA $2,523~~
CA $2,062
per traveller
found 2 hours ago
Brisas del Mar, Inn at the Beach
Jan 18 - Jan 22
Lavender Inn by the Sea + Flight
Santa Barbara Beach
4 nights
3.5 star property
9.2/10 - Wonderful (1,359 reviews)
"The location couldn’t be better, close to downtown and the harbor. The staff clearly care about the property and experience of their guests. Everyone was kind and the room and community spaces are lovely and welcoming. Be prepared for many LED light displays on electronics (power strips, clock, microwave) you might not notice until it’s bedtime, but that is a non issue for most and can be easily solved with strategically draped towels."
Reviewed November 5, 2026
Roundtrip • Kamloops (YKA) - Santa Barbara (SBA)
YKA - SBA • 2 stops SBA - YKA • 2 stops
~~CA $2,352~~
CA $1,982
per traveller
found 2 hours ago
Lavender Inn by the Sea
Jan 18 - Jan 22
Inn By The Harbor + Flight
Santa Barbara Beach
4 nights
3.5 star property
9.2/10 - Wonderful (1,963 reviews)
"Five stars all the way. Loved our room, and management upgraded our room."
Reviewed November 5, 2026
Roundtrip • Kamloops (YKA) - Santa Barbara (SBA)
YKA - SBA • 2 stops SBA - YKA • 2 stops
~~CA $2,326~~
CA $2,007
per traveller
found 0 hours ago
Inn By The Harbor

Where to stay in Winchester

Find the best Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Winchester

A rocky shoreline with waves crashing against the rocks.

Isla Vista

You'll enjoy the beaches and live music in Isla Vista. You might want to make time for a stop at Isla Vista Beach or UC SB Events Center.

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A coastal cityscape with Mediterranean architecture, palm trees, and a clear sky.

Old Town

Old Town might not have many top sights, but Goleta Beach and Isla Vista Beach are two attractions nearby that you can check out.

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A railway track running alongside a beach with mountains in the background.

Gaviota

If you're spending some time in Gaviota, Gaviota Beach and Gaviota State Park are top sights worth seeing.

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Ellwood

While visiting Ellwood, you might make a stop by sights like Sandpiper Golf Club and Goleta Butterfly Grove.

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A historic building with a bell tower, arches, and a fountain.

Fairview

If you're spending some time in Fairview, Center for Urban Agriculture at Fairview Gardens and Zodo's - Bowling and Beyond are top sights worth seeing.

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