A church with two domes and a cross in front.
Photo by David Simmington
Open Photo by David Simmington

Upper East Vacations from $893

Book a Hotel + Flight or Car together to unlock savings

Your Upper East Vacation

Planning your next exciting getaway just got easier with a vacation package to Upper East. Embrace the very best this neighborhood has to offer while creating fond memories you'll treasure. Not sure what to do during your trip to Upper East? Nearby attractions like Santa Barbara County Courthouse, Mission Santa Barbara and Presidio Santa Barbara are excellent places to start. No matter what your dream Upper East vacation may look like, you can turn it into reality with Expedia.

The Latest Upper East Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A patio with striped sofas and a table, overlooking a beach with palm trees and flowers.
    Jan 23 - Jan 28

    The Milo + Flight

    Santa Barbara Beach
    5 nights
    4.0 star property
    8.6/10 - Excellent (1,619 reviews)
    "Great stay. See you next time."
    Reviewed November 8, 2026
    Roundtrip • Chicago (CHI) - Santa Barbara (SBA)
    ORD - LAX • Nonstop LAX - ORD • 1 stop
    Save 100% on your flight
    $1,241
    $893
    per traveler
    found 1 day ago
    The Milo
  • A small building with a tiled roof surrounded by lush greenery and flowering plants.
    Jan 23 - Jan 28

    El Encanto Santa Barbara + Flight

    Upper Riviera
    5 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 • Chicago (CHI) - Santa Barbara (SBA)
    ORD - SBA • 1 stop SBA - ORD • 1 stop
    Save 100% on your flight
    $2,610
    $1,753
    per traveler
    found 1 day ago
    El Encanto Santa Barbara
  • A modern kitchen with wooden cabinets, a central island, and large windows.
    Jan 23 - Jan 28

    Drift Santa Barbara, a Member of Design Hotels + Flight

    Downtown Santa Barbara
    5 nights
    3.5 star property
    8.4/10 - Very good (508 reviews)
    Roundtrip • Chicago (CHI) - Santa Barbara (SBA)
    ORD - SBA • 1 stop SBA - ORD • 1 stop
    Save 100% on your flight
    $1,312
    $904
    per traveler
    found 1 day ago
    Drift Santa Barbara, a Member of Design Hotels
  • A large, two-story building with a tiled roof, surrounded by palm trees and a well-maintained garden.
    Jan 23 - Jan 28

    Inn By The Harbor + Flight

    Santa Barbara Beach
    5 nights
    3.5 star property
    9.2/10 - Wonderful (1,968 reviews)
    Roundtrip • Chicago (CHI) - Santa Barbara (SBA)
    ORD - SBA • 1 stop SBA - ORD • 1 stop
    Save 100% on your flight
    $1,327
    $959
    per traveler
    found 1 day ago
    Inn By The Harbor
  • A multi-story building with a curved entrance, palm trees, and a staircase leading to the entrance.
    Jan 23 - Jan 28

    Brisas del Mar, Inn at the Beach + Flight

    Santa Barbara Beach
    5 nights
    3.5 star property
    9.4/10 - Exceptional (1,463 reviews)
    "I would highly recommend this property, friendly staff, free happy hour, free breakfast, free bicycle, centrally located, clean, friendly"
    Reviewed November 7, 2026
    Roundtrip • Chicago (CHI) - Santa Barbara (SBA)
    ORD - SBA • 1 stop SBA - ORD • 1 stop
    Save 100% on your flight
    $1,452
    $1,058
    per traveler
    found 1 day ago
    Brisas del Mar, Inn at the Beach

Where to stay in Upper East

Find the best Upper East areas and neighborhoods for the activities you enjoy most.
A coastal town with a pier extending into the ocean, a beach, and a mix of residential and commercial buildings.

Santa Barbara Beach

Santa Barbara Beach is known for its stunning beaches, and you can see some sights in the area like Stearns Wharf and West Beach.

A beach with a pier, buildings, and mountains in the background.

Montecito

Celebrity-favored Montecito offers backcountry hiking trails and attractions like Lotusland and El Fureidis. Easily accessible via State Route 192 and the U.S. 101 Freeway, it's well-connected to Santa Barbara County.

A white colonial building with a bell tower, surrounded by palm trees and a clear blue sky.

Downtown Santa Barbara

The pristine beaches and ample dining options are top of the list for many visitors to Downtown Santa Barbara. A stop by Lobero Theater or Presidio Santa Barbara might round out your trip.

A beach with a pier extending into the water, mountains in the background, and several flags on the pier.

West Beach

While visiting West Beach, you might make a stop by sights like Santa Barbara Harbor and West Beach.

A beach with palm trees, a pier, and the ocean at sunset.

East Beach

East Beach is known for its stunning beaches, and you can see some sights in the area like East Beach and Santa Barbara Zoo.

Discover the most popular places to visit in Upper East

A historic church with a bell tower and a fountain in the foreground.
Photo by Leonardo De Leon
Open Photo by Leonardo De Leon

Mission Santa Barbara

9.2/10 (1,948 reviews)
Learn about the local history of Santa Barbara with a stop at Mission Santa Barbara. Wander the beautiful beaches and seaside in the area.
See properties

What to do near Upper East

Coastal Cruise on Yacht in Santa Barbara

Coastal Cruise on Yacht in Santa Barbara

$38
per adult
98% of travelers recommend
Coastal Cruise on Yacht in Santa Barbara
See all activities near Upper East

Upper East Hotel Deals

A poolside area with lounge chairs and a small table, a stone planter, and a pool with a tiled edge.

Orange Tree Inn

Orange Tree Inn
2.5 star property
Upper East
7.8 out of 10, Good, (941 reviews)
$100 nightly
The price is $114
Nov 18 - Nov 19
Total with taxes and fees
Orange Tree Inn
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.
See all properties in Upper East
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.