Upper East Holidays

Photo by Rachel M
    deals illustration

    Better together

    Save up to S$134 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Upper East

Find the best Upper East areas and neighborhoods for the activities you enjoy most. Learn more about Upper East
Default Image

Montecito

1 out of top 10 points of interest in this area
5/5(4 area reviews)

The pristine beaches and ample dining options are top of the list for many visitors to Montecito. A stop by Miramar Beach or Butterfly Beach might round out your trip.

Find hotels in Montecito

Top hotels in Upper East

Orange Tree Inn
Orange Tree Inn
2.5 out of 5
1920 State Street, Santa Barbara, CA
Fully refundableReserve now, pay when you stay
The price is S$141 per night from 27 Jul to 28 Jul
S$141
27 Jul - 28 Jul
includes taxes & fees
7.4/10 Good! (649 reviews)
"Great little hotel. Clean, well kept. Would absolutely stay again."

Reviewed on 8 Jul, 2025

Orange Tree Inn
Simpson House Inn
Simpson House Inn
5 out of 5
121 East Arrellaga Street, Santa Barbara, CA
Fully refundableReserve now, pay when you stay
The price is S$467 per night from 15 Jul to 16 Jul
S$467
15 Jul - 16 Jul
includes taxes & fees
9.8/10 Exceptional! (659 reviews)
"Loved it! Great hidden gem."

Reviewed on 12 Jul, 2025

Simpson House Inn
The Milo
The Milo
3.5 out of 5
202 W Cabrillo Blvd, Santa Barbara, CA
Fully refundableReserve now, pay when you stay
The price is S$475 per night from 20 Jul to 21 Jul
S$475
20 Jul - 21 Jul
includes taxes & fees
8.2/10 Very Good! (1,387 reviews)
"Loved the beachfront location and ability to use the property’s bikes to explore the local area. The room was comfortable and had plenty of space for our one night stay. We only used one pool area but found it clean and warm. Really lovely stay and would definitely return!"

Reviewed on 10 Jul, 2025

The Milo
See all 1,538 properties in Upper East
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.

Frequently asked questions

How much does an Upper East holiday package cost?
Our Upper East packages, which begin at just , are an awesome way to save big bucks. Handpick your preferred hotels, flights and rental car to create your ideal itinerary.
How do I get a cheap travel package to Upper East?
Find flights that fit your busy schedule, add a hotel to your booking and watch the savings grow with an Upper East holiday package. It's as easy as that! From flights and hotels to rental cars and activities, Expedia makes travelling on a budget easy. And with more than 550 air carriers and 1,000,000 hotels across the globe to choose from, you won't be short of choice.
Where should I stay in Upper East?
A trip to Upper East has to include Mission Santa Barbara and Santa Barbara County Courthouse. Stay somewhere close by for easy access to these awesome attractions.
What are the top hotels in Upper East?
Orange Tree Inn and Simpson House Inn are among the most popular hotels in Upper East. Why not check out the facilities and rates at each and then decide?
How far in advance should I book my Upper East holiday?
Smart travellers will likely want to book as early as possible. You can normally compare international fares on Expedia up to 12 months before your flight. If you've left booking to the last minute, don't stress. Bargain prices occasionally occur just weeks before departure dates.
What does an Expedia Upper East travel package include?
Hotels, rental cars and flights --- we've got them all. With Expedia, you can shape your Upper East travel package however you want. All you have to do is determine just what you need. Once you've made your booking, you can add on fun things like tours and activities. The more you bundle, the more you save!
What should I know before booking an Upper East travel package?
An Expedia travel package can be tailored to your budget and is a terrific way to stretch your dollars further. What you include is completely up to you. Hotels, rental cars and flights --- come up with a combination that suits your style.
Can I choose my airline with an Upper East Expedia holiday package?
With a holiday package, you're the one in charge. Whether you're looking to fly to Upper East in coach or first class, simply choose from the available airline options. Expedia has access to over 550 partner airlines across the world.
If I'm not able to travel, can I cancel my Upper East holiday package?
Whether it's your flight or hotel, yes, you can cancel or amend it. Locked in your Upper East holiday package in the last 24 hours? You may be able to make changes or cancellations at no cost. For bookings older than that, you may be charged a fee by your hotel, airline or car rental company. For further information, take a look at our Customer Service Portal. We're here to help you every step of the way.

Things to do

Santa Barbara Trolley Tour

Santa Barbara Trolley Tour

S$36
per adult
86% of travellers recommend
Santa Barbara Trolley Tour
Santa Barbara Highlights Private 2-Hour Driving Tour

Santa Barbara Highlights Private 2-Hour Driving Tour

S$58
per traveller
Santa Barbara Highlights Private 2-Hour Driving Tour
Best of Santa Barbara: A Stroll Through Paradise

Best of Santa Barbara: A Stroll Through Paradise

S$657
per adult
Best of Santa Barbara: A Stroll Through Paradise
See all activities in Santa Barbara

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.