Winchester Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Winchester Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Inn By The Harbor
Santa Barbara Beach
Price was $1,772, price is now $1,296 per person
$1,296
per person
Aug 17 - Aug 21
found 4 hours ago
Roundtrip non-stop flight included
Peoria (PIA) to Santa Barbara (SBA)
Book a stay at this business-friendly hotel in Santa Barbara. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Santa Barbara Harbor and Santa Barbara Bowl are located nearby.
Hotel Santa Barbara
Downtown Santa Barbara
Save 100% on your flight
Price was $2,476, price is now $1,677 per person
$1,677
per person
Sep 8 - Sep 15
found 5 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Santa Barbara (SBA)
Book a stay at this business-friendly hotel in Santa Barbara. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Santa Barbara Harbor and Santa Barbara Bowl are located nearby.
Lavender Inn by the Sea
Santa Barbara Beach
Save 100% on your flight
Price was $2,023, price is now $1,483 per person
$1,483
per person
Sep 8 - Sep 15
found 5 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Santa Barbara (SBA)
Book a stay at this business-friendly hotel in Santa Barbara. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Santa Barbara Harbor and Stearns Wharf are located nearby.
El Encanto Santa Barbara
Upper Riviera
Save 100% on your flight
Price was $4,416, price is now $3,277 per person
$3,277
per person
Sep 8 - Sep 15
found 5 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Santa Barbara (SBA)
Book a stay at this luxury hotel in Santa Barbara. Enjoy free WiFi, a full-service spa, and 2 restaurants. Popular attractions Santa Barbara Bowl and Santa Barbara Harbor are located nearby.
Brisas del Mar, Inn at the Beach
Santa Barbara Beach
Price was $1,772, price is now $1,315 per person
$1,315
per person
Aug 17 - Aug 21
found 4 hours ago
Roundtrip non-stop flight included
Peoria (PIA) to Santa Barbara (SBA)
Book a stay at this business-friendly hotel in Santa Barbara. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Santa Barbara Harbor and Stearns Wharf are located nearby.
Mar Monte Hotel, in The Unbound Collection by Hyatt
Santa Barbara Beach
Save 100% on your flight
Price was $1,983, price is now $1,510 per person
$1,510
per person
Sep 8 - Sep 15
found 5 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Santa Barbara (SBA)
Book a stay at this beach hotel in Santa Barbara. Enjoy free WiFi, 2 restaurants, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Santa Barbara Zoo and Stearns Wharf are located nearby.
Top Hotel Deals
Hotel Santa Barbara
533 State St Santa Barbara CA
17.77 km from Winchester
Book a stay at this business-friendly hotel in Santa Barbara. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff ...
Ramada by Wyndham Santa Barbara
4770 Calle Real Santa Barbara CA
9.3 km from Winchester
Book a stay at this business-friendly hotel in Santa Barbara. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the pool and the ...
Sandpiper Lodge
3525 State St Santa Barbara CA
13.73 km from Winchester
Stay at this motel in Santa Barbara. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Avania Inn of Santa Barbara
128 Castillo St Santa Barbara CA
18.01 km from Winchester
Book a stay at this business-friendly motel in Santa Barbara. Enjoy free WiFi, free parking, and premium TV channels. Our guests praise the breakfast and the ...
Beachside Inn
336 W. Cabrillo Blvd Santa Barbara CA
18.19 km from Winchester
Stay at this hotel in Santa Barbara. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
The Franciscan Hotel
109 Bath Street Santa Barbara CA
18.12 km from Winchester
Book a stay at this business-friendly hotel in Santa Barbara. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and ...
Inn By The Harbor
433 W Montecito St Santa Barbara CA
17.78 km from Winchester
Book a stay at this business-friendly hotel in Santa Barbara. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool ...
Wine Valley Inn
1564 Copenhagen Dr Solvang CA
29.13 km from Winchester
Book a stay at this spa hotel in Solvang. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hilton Santa Barbara Beachfront Resort
633 E Cabrillo Blvd Santa Barbara CA
19.56 km from Winchester
Book a stay at this beach resort in Santa Barbara. Enjoy a full-service spa, 2 restaurants, and 6 outdoor pickleball courts. Our guests praise the helpful staff ...
Chumash Casino Resort
3400 East Highway 246 Santa Ynez CA
26.36 km from Winchester
Book a stay at this spa resort in Santa Ynez. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
The Milo
202 W Cabrillo Blvd Santa Barbara CA
18.35 km from Winchester
Book a stay at this beach hotel in Santa Barbara. Enjoy free WiFi, 2 outdoor pools, and free bicycles on site. Our guests praise the helpful staff and the clean ...
Santa Barbara Inn
901 E Cabrillo Blvd Santa Barbara CA
20.02 km from Winchester
Stay at this hotel in Santa Barbara. Enjoy free WiFi, room service, and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. ...
The Ritz-Carlton Bacara, Santa Barbara
8301 Hollister Avenue Goleta CA
2.88 km from Winchester
Book a stay at this luxury resort in Goleta. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Aug 13 - Sat, Aug 29
PHX
Sky Harbor Intl.
SBA
Santa Barbara Municipal
$223 Roundtrip, found 1 day ago
$223
Roundtrip
found 1 day ago
Sat, Oct 17 - Tue, Oct 20
PDX
Portland Intl.
SBA
Santa Barbara Municipal
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Sat, Oct 17 - Tue, Oct 20
PDX
Portland Intl.
SBA
Santa Barbara Municipal
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Sat, Oct 17 - Tue, Oct 20
PDX
Portland Intl.
SBA
Santa Barbara Municipal
$237 Roundtrip, found 1 day ago
$237
Roundtrip
found 1 day ago
Sat, Oct 17 - Tue, Oct 20
PDX
Portland Intl.
SBA
Santa Barbara Municipal
$267 Roundtrip, found 1 day ago
$267
Roundtrip
found 1 day ago