Winchester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Holiday Package Deals in Winchester
Price found within the past 48 hours. Click for updated prices.
Inn By The Harbor
Santa Barbara Beach
Price was CA $2,920, price is now CA $2,305 per person
CA $2,305
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Santa Barbara (SBA)
9.2/10 Wonderful! (1,897 reviews)
Beautiful gardens, walkable to favorite areas and nice breakfast in the am. With wine & cheese & cookies in the afternoon…what more do you need.
Reviewed on Jun 20, 2026
Hotel Santa Barbara
Downtown Santa Barbara
Price was CA $3,548, price is now CA $2,622 per person
CA $2,622
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Santa Barbara (SBA)
9.4/10 Exceptional! (1,396 reviews)
Loved the location! Staff was super friendly and helpful! Will stay here again for sure!
Reviewed on Jun 21, 2026
Brisas del Mar, Inn at the Beach
Santa Barbara Beach
Price was CA $2,988, price is now CA $2,368 per person
CA $2,368
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Santa Barbara (SBA)
9.4/10 Exceptional! (1,426 reviews)
A little noisy for my liking
Reviewed on Jun 14, 2026
El Encanto Santa Barbara
Upper Riviera
Price was CA $6,191, price is now CA $4,928 per person
CA $4,928
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Santa Barbara (SBA)
9.4/10 Exceptional! (571 reviews)
Beautiful location up in the hills , views , quiet , relaxing . Staff is very friendly and helpful .
Pool was great , very very clean . Food was good , I recommend the short ribs ♥️♥️one of the best I’ve had . It was a wonderful little weekend get away , I will definitely be going back , loved it !
Reviewed on May 31, 2026
Lavender Inn by the Sea
Santa Barbara Beach
Price was CA $2,906, price is now CA $2,318 per person
CA $2,318
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Santa Barbara (SBA)
9.2/10 Wonderful! (1,367 reviews)
Nice afternoon wine and cheese reception. Very nice breakfast.
Walkable to harbor.
Reviewed on Jun 21, 2026
Where to stay in Winchester
Find the best Winchester areas and neighborhoods for the activities you enjoy most. Learn more about Winchester
Isla Vista
3 out of top 10 points of interest in this area
You'll enjoy the beaches and live music in Isla Vista. You might want to make time for a stop at UC SB Events Center or Isla Vista Beach.
Winchester Hotel Deals
Hotel Santa Barbara
533 State St Santa Barbara CA
Fully refundableReserve now, pay when you stay
The price is CA $365 per night from Jul 6 to Jul 7
CA $365
CA $425 total
Jul 6 - Jul 7
includes taxes & fees
9.4/10 Exceptional! (1,405 reviews)
"Loved the location! Staff was super friendly and helpful! Will stay here again for sure!"
Reviewed on Jun 21, 2026
Ramada by Wyndham Santa Barbara
4770 Calle Real Santa Barbara CA
Fully refundableReserve now, pay when you stay
The price is CA $300 per night from Jul 23 to Jul 24
CA $300
CA $348 total
Jul 23 - Jul 24
includes taxes & fees
8.8/10 Excellent! (1,208 reviews)
"Breakfast was sparse and not the best. Room was way too small, not worth the incredibly high prices."
Reviewed on Jun 21, 2026
Sandpiper Lodge
3525 State St Santa Barbara CA
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Jul 20 to Jul 21
CA $184
CA $210 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (2,499 reviews)
"Clean room"
Reviewed on Jun 22, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Winchester
Devereaux Slough
Enjoy an outing to Devereaux Slough during your stay in Goleta. Attend a sporting event in this walkable area, or seek out the biking trails.
Things to do
Santa Barbara: Beach and Coastline Helicopter Tour
CA $96
per adult
Santa Barbara Vineyard to Table Taste Tour by E-Bike
CA $275
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.